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p. 23. Last paragraph, line 2. The name of 1.63 is incorrect.
It should be 4-methylhex-5-en-1,3-diol
p. 30. Paragraph beginning with In Chap. 4 .....- line 3.
Change 1.72 to 1.74
line 5. Change 1.74 to 1.73
p. 32. As drawn, 1.83 has no chiral centers. The correct structures should
nclude methyl groups. It should be -
Likewise, structures 1.86 and 1.87 must include methyl groups since
as drawn, they do not contain a chiral enter.
These structures should be -
p. 50. In structure 1.185 - the Zn should be connected to B, not H.
p. 51. Second paragraph - line 1. Change "both" to "E,E". It should read
......is substituted, E,E, Z,E and E,Z dienes are possible.
p. 55. Last paragraph - line 4. Delete Although there are two chairs. It
should read
.......and the C5-4-3-6-7 ring. In 1.208, there is a boat-like ......
p. 74. Lines 4,5,6. Line 4 - Change 1.272 to 1.278.
Line 5 - Change 1.272 to 1.278.
Line 6 - Change 1.273 to 1.279
p. 82. Structures 1.324 and 1.326 have a bond at C-7 which is not
supposed to be there. The stereochemistry in the D-ring of
1.324 is beta. The OH in the D-ring of 1.326 should be beta,
not alpha as shown. The correct structures are -
p. 83. Reference. 14(c). Spelling. Schöllkopf, U.
Reference. 20. Spelling. Helmchen
p. 99. First paragraph - line 1. Change acidity to basicity. This should read
.....The trend in basicity based on rule (c) is that basicity increases .......
- line 5. Change ...C-I bond ... to ....H-I bond .....
p. 105. line 13. Change nonane to non-5-ene. It should read
... 1,3-diazabicyclo[4.3.0]non-5-ene (DBN, 2.20)
line 14. Change 1,5 to 1,8 and undecane to undec-7-ene.
It should read
1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 2.21)
p. 111. Under item 1. Change more to less. It should read
1. Heavier and less electronegative members of a series are usually softer
. Table 2.4. Under Hard Acids. 2nd row. change Gd+3 to Gd+3
Mid page. Change sp3 and sp labels.
It should be sp3 C > sp2 C > sp C
p. 114. Last paragraph after I and A formulas - line 4. Change Figure 2.2 to Figure 2.1
p. 116. Figures at the top of the page. Under Rule (2), the "products" are mislabeled.
"Nu" should be Sb and "E" should be HA. They should be -
p. 172. The propenyl group in 2.235 is on the wrong carbon. The
structure should be -
line 26. Change 5ß to 5alpha. It should be
....that the 5alpha isomer
p. 180. For the conversion of 2.274 to 2.275, the reagent over the arrow
is not Hg(OAc)4. It should be mercuric acetate - Hg(OAc)2
p. 183. The positive charge on chlorine is missing from structure 2.288.
It should be -
p. 185 Structure 2.301, Change Cr to Cl. It should be -
p. 187. The structure in front of 2.307 is phenanthrene.
The C7-C8 bond should be C=C, not C-C.
p. 195. Structure 2.345. The "right" resonance structure is
incorrect. There should be a N=C bond, not a N-C bond.
p. 201. REFERENCE. Under 70. Spelling. Kharasch, M.S.
p. 209. Under 12(b). Structure 4 should be a sulfoxide with a S=O unit.
p. 222. The formula after the second paragraph (begins with 3 equiv. of
2-propanol), contains 8 H2C at the end of the equation. This is
incorrect. It should be + 8 H2O
p. 241. Note - not in text. The Dess-Martin reagent can be shock
sensitive under some conditions and explode above 200 degress C. See
Chem. Eng. News, 1990, July 16, p. 3. For an improved procedure -
see J. Org. Chem., 1993, 58, 2899.
p. 258. Structure 3.160 is missing a double bond. It should be -
p. 265. Entry 2 in Table 3.5. Under M %, add MoO3 (12)
p. 267. First line - Delete C from 50 degress C. It should read
.....about 50 degrees. This model predicts ......
The oxygen in 3.188 connected to CMe3 requires a positive charge
Structure 3.189 requires a negative charge on one oxygen and a
positive charge on the epoxide-oxygen. These structures should be -
p. 272. Change a Me group for H in structures 3.214 and 3.215. They
should be -
p. 280. Structure 3.240 is missing an R group. It should be -
p. 282. First paragraph - line 9. Change 3.246 to 3.247
p. 286. In 2nd paragraph and in all cases. Change from asymmetric
hydroxylation to asymmetric dihydroxylation.
p. 292. Last paragraph - line 6. Change...enophile to ...diene.
It should read
......was used as a diene (see Chap. 11, ......
p. 300. Last paragraph - line 1. Delete ketone products and replace with
aldehydes. It should read
....alkenes leads to aldehydes, but if the alkenyl ......
p. 309. First paragraph after top structures - line 1. Change 3.371
to 3.364
p. 311. Third paragraph - line 3. Compound 3.382 is not a selenol. This
should read
....affords 3.382, which is hydrolyzed to the allylic .......
p. 320. Last paragraph - line 3. Change 1-thioalkyl to 1-alkylthio
- line 19. Change monoperoxycamphonic to monoperoxycamphoric
p. 322. Line 2. Change toluene to tolyl
p. 344. First paragraph, line 8 - change reducing to oxidizing. It
should read (Li+ is a very poor oxidizing agent)
First paragraph, line 9 - change Sn+4 to Sn+2
p. 346. Last paragraph - line 5. Add "O is". It should read
......hydride (O is polarized .....
Last paragraph - line 6. Add "C is". It should read
.....carbonyl (C is polarized ......
p. 347. First paragraph - lines 3,4. Change 4.6 to 4.7, and change this
sentence to include the
number of moles of each reactant. It should read -
.......In principle, four moles of acetone reacts with four equivalents
of hydride (1 mole) to give 4.7.........
The numbers 4.5 and 4.6 should be under the structures -
not under the reaction arrows.
p. 349. Structure 4.18 is missing a carbon. It should be -
p. 350. Second paragraph - line 7. Change "a" to "2". It should read
.....bearing an heteroatom at the 2-position is also possible.
The LiAlH4 reaction in mid-page gives a product 2 LiAlO2
not LiAlO23
p. 352. In the reaction sequence on the bottom of the page, all
Al species have a negative charge.
p. 353. First paragraph - line 6. Substituents is misspelled. diminished
by substituents.
Second paragraph - line 12. Replace benzyl with benzoyl.
It should read
........of an amine with benzoyl chloride or
p. 354. Second paragraph - line 4. Change C-O bond to C=O moiety.
It should read
......with cleavage of the C=O moiety to give a .......
Second paragraph - line 9. Add a phrase to the end of the sentence. It should read
..... a benzylic alcohol upon reduction of a benzyl carbamate.41
p. 356. Last paragraph - line 3. The way SN2 is written is not exactly
correct. It should be as shown here.
p. 357. Last paragraph - line 5. Change this sentence. It should read
......amino group (RN3 to RNH2), which was then treated with
benzoyl chloride to give 4.65, and this was a key step in ........
p. 358. First paragraph - lines 3 and 12. Change diazo to azo
Last paragraph - line 5. This would be better if it read
....... (4.74, cosmene) via addition of 4 H followed by formal
elimination .........
p. 359. Last paragraph - line 8. add the word primary. It should read
.........of diol 4.79 to the primary monotosylate and reduction.....
p. 360. The "bottom" bicyclic structures in 4.82 and 4.83 do not contain
methyl groups and should contain a double bond. The structures
should be -
p. 362. First paragraph - line 11. Remove the word hydride. It should read
.......to form lithium tetramethoxyaluminum [LiAl(OMe)4], but three .......
Last paragraph - line 20. remove the -amide. It should read
..N,N-diethyl analog of 4.88
- line 21. Remove -amide derivative. It should read
.....and the N,N-diisopropyl analog
p. 364. First paragraph - line 5,6. Change this to read
....as in the conversion of methyl p-chlorobenzoate to
p-chlorobenzaldehyde (-22 degrees C for 8 hr) in 77% yield.82
p. 365. Last paragraph - line 6. add the word "yield". The sentence
should read
.....example, in 99% yield).96
p. 371. Last paragraph - last line. Add "after hydrolysis". It should read
......aldehyde, after hydrolysis, in this case ...........
p. 372. The PHCH2O- in structure 4.141 should be PhCH2O-
p. 380. Second paragraph - line 3. Add "thio-" and change thioethyl. It should read
(derived from thio-lactam 4.186) to the ethylthio......
Last paragraph - line 9. move 4.193. The sentence should read
....to the syn-alcohol, for example, which was then trapped as the
acetate (4.193), in 70% .....
p. 381. Second paragraph - line 7. Change 4.203 to 4.198
- lines 8,9. Spelling titanium
p. 382. Last paragraph - first line after equation. Change 'above' to
'less acidic than'. It should read
.....decompose in acid solution (less acidic than about pH 3).
p. 385. Entry 9 in Table 4.4. The structure is incorrect - add a carbon.
It should be MBH(O2CR)3
p. 386. The fast/slow labels on the reactions are reversed. The conversion
of 4.212 to 4.213 should be labeled SLOW. The conversion
of 4.214 to 4.215 should be labeled FAST.
p. 387. Second paragraph - last line. Change phenylalinol
to phenylalaninol
p. 389. Last paragraph - line 3. The structure for Dibal is incorrect.
It should be ([(CH3)2CHCH2]2AlH, Dibal),
p. 392. Line 26. The structure labeled Darvon is actual Darvon alcohol.
Darvon is the -O2CEt ester of this alcohol.
Line 27. Change the word enantiomer to diastereomer.
p. 393. The structures of 4.248 and 4.249 are incorrect. Acetonides are
shown rather than cyclohexylidene derivatives. They should be -
p. 394. Structure 4.250 is incorrect. It should be -
Second paragraph - line 3. Add 'alcohol'. It should read
.....Mosher (Darvon alcohol is 4.250)
Last paragraph - lines 3 and 7. Change (1R,2S,3R,5R)
to (1R,2S,3S,5S)
p. 395. First line - change [4.4.1] to [3.3.1]
Last paragraph - lines 5,6. Delete 'in diglyme'. Change
-methyl-2-propanone to 2-methyl-3-pentanone. These
sentence should read
..........gave 14% ee [(R)-phenethyl alcohol]. Similar reduction of
ethyl isopropyl ketone (2-methyl-3-pentanone) gave 62% ee of the ...
p. 396. Line 7. Change cysteine to cystine. It should read
N,N'-dibenzoylcystine
p. 400. Structure 4.272 is missing a methylene group. - These structures
should be -
Second paragraph - line 6. Change 4.275 to 4.276
Second paragraph - line 10. The term racemic is misleading here.
The new chiral center will be racemic, but the chiral center at C-7
(where the Ph is attached) remains intact.
NOTE - not in text. Alcohols 4.277 and 4.278 are diastereomers, and both are racemic.
p. 403. Last paragraph - line 16. Change hydroxyl to methoxy. It
should read
....The presence of the methoxy group in 4.291 led ......
p. 406. First paragraph - line 3. Change 4.301 to 4.299b
p. 408. Compound 4.312 is mislabeled. It should be numbered 4.311
p. 409. The left R group should be labeled RL. It should be -
p. 413. First paragraph - line 3. Change Attach to Attack. It
should read.
......making path a preferred. attack via path a leads to ...........
p. 414. Line 4. make hydrogen plural. It should read
......inhibited by the axial hydrogens on the 'bottom' ..........
p. 415. Last paragraph - line 4. Change 4.350 to 4.349
- line 5. Change 4.349 to 4.350
p. 418. First paragraph - line 2. Lusche is a misspelling.
It should be Luche.
p. 421. The steroid structures 4.371 and 4.372 are drawn with a
six-membered D-ring. This is incorrect. Both should have a
five-membered D-ring. These structures should be -
p. 427. Second paragraph - line 20. heteroatom should be singular. It
should read
.......show less reactivity with heteroatom-containing
functional groups, ..............
p. 429. Structure 4.391 should be a pi-complex. It should be -
pp. 431-432. For the hydrogenation of 4.408 - product 4.409 is the result of cis-delivery of
hydrogen when focused on the bridgehead methyl, but not when focused on the
methyl alpha- to the carbonyl. It should be
At the top of p. 432 - line 4, this should read -
......where the trans-relationship of the methyl alpha- to the carbonyl and the ring
juncture hydrogen is clearly not the result of the expected cis-delivery of hydrogen.
p. 434. First paragraph - line 2. Change anti to syn. It should read
....the syn isomer (4.412).
p. 436. The palladium on barium sulfate catalyst, poisoned with quinoline,
referred to on the middle of this page can be called the Rosenmund catalyst.
For the conversion of 4.425 to 4.426, the EtAc over the reaction
arrow should be ethyl acetate, EtOAc.
p. 441. First paragraph - line 6. Change aniline to benzylamine.
It should read
.......nitrile moiety of the benzylamine derivative with platinum.
p. 444. NOTE. The hydrogenation of benzene to cyclohexane shown on
p. 444 should be on p. 445, just above the hydrogenation of
naphthalene to give 4.468.
p. 446. The two structures labeled 4.476 are not resonance structures -
they are in equilibrium. These structures should be -
p. 447. Structure 4.484 is incorrect. Replace the Me group on the chain
with a butyl group. It should be -
p. 448. First major paragraph - line 8. change ethylmenthoxy to
l-menthoxyacetate.
p. 449. First paragraph - line 3. add "be". It should read
....the enantioselectivity can be very good, .......
p. 451. Second paragraph - line 13. change 'a proton" to "an hydrogen
atom". It should read
.....or it can remove an hydrogen atom from an acidic solvent .........
Structure 4.504 is missing a negative charge on the oxygen of the
first resonance form.
p. 452. First new paragraph - lines 1,2. Change non to oct.
It should read
....formation of 4,5-octanediol in 55% ..........
p. 453. First paragraph - line 4. Change with to containing. It should read
.....in a methylamine solution containing LiCl ....
Second paragraph - line 7. Change propane to propene.
It should read
......2-Methylpropenenitrile, for example, .......
Last paragraph - line 2. Change 4.536 to 4.518
and 4.537 to 4.519
p. 456. Last paragraph - last line. Change hydrogen to proton.
It should read
....A second proton is transferred ......
pp. 458-459. Last paragraph on p. 458 - last line. Only one equivalent
of sodium is required. See J. Am. Chem. Soc., 1943, --, 2020.
p. 463. Last paragraph - lines 8,9. group and carbon should be plural.
This should read
.....withdrawing COOH groups on the saturated carbons in 4.584.
p. 467. Second paragraph - lines 5,6. Change 4.635 to 4.612.
Change 4.613 to 4.610. It should read
.....and 35% of 4.612 after addition of 4.610 to the amine solution ....
Second paragraph - line 10. Change 'a quantitative" to an 89%.
It should read
.....ethylenediamine gave an 89% conversion to 4.611 .....
Last paragraph - last line. Change dibromoester to bromoester.
p. 469. Line 2. Clemmensen is misspelled. Delete the "o" and replace
with "e".
p. 470. Last paragraph - line 11. change unspecified to 73% overall.
It should read
......aldehyde (4.634) in 73% overall yield.
p. 472. Second paragraph - line 4. change phenylsulfone
to phenylsulfonyl
p. 473. Second paragraph - line 2. Clemmensen is misspelled.
Second paragraph - line 17. Change structure to -CH2-NR-CH2-
p. 475. Second paragraph - line 4. Change 4.658 to 4.659
p. 476. Last paragraph - line 7. Delete a "2". It should read
.......and 3-(-)-erythro-2-(N-methyl)pyrrolidiniminiumbutanoic acid
(4.664) was .......
p. 478. Last paragraph - line 2. Delete the word "reductively".
It should read
.......that the iodide in 4.675 is cyclized (via 4.676) in the ..........
p. 479. Second paragraph - line 10. Change latter to former.
It should read
.......(HDLADH). This former reagent is usually obtained from yeast ......
p. 497. REFERENCE. for 501 (a). Spelling. Clemmensen, E.
p. 499. HOMEWORK. For both 1(c) and 1(d), this problem makes more
sense if the starting materials are methyl ketones rather than
aldehydes. In both cases, delete the O=C-H unit and replace it
with O=C-Me.
p. 538. Change structure number 4.147 (bottom of page) to 5.147
p. 567. HOMEWORK. For 5(b). Delete 2-ethyl-3-hexene. Replace it
with E-6-methyl-3-octene.
p. 588. Both structures 6.103 and 6.104 appear to have a double bond.
They are both decalin derivatives with two saturated
six-membered rings.
The negative charge for both 6.107 and 6.108 are on the
wrong side of the carbonyl. An extra arrow also appears in
6.108. The correct structures should be -
p. 596. First paragraph - line 3. Change tertiary to secondary.
It should read
.......mixture of diastereomeric secondary alcohols ......
p. 599. Last paragraph - line 3. Change 6.178 to 6.172
p. 600. Third paragraph - line 6. Change "of" to "to". It should read
......membered ketal to 6.182, which has the more ......
p. 603. Second row of structures. Change 5-exo-tet to
5-endo-tet. Change 6-exo-tet to 6-endo-tet.
p. 604. First major paragraph - lines 13,14. Change 6.200 to 6.202
and change 6.201 to 6.200. This should read
.......closure of 6.199 to 6.20260 via radical intermediates such as
6.200 (see .......
Last paragraph - line 7. Change "endo" to "intramolecular".
It should read
.......For intramolecular reactions, attack at ........
p. 606. Last paragraph - lines 1,2. Change "dig" to "trig".
It should read
.......the 5-exo-trig product (6.213) was favored over the 6-endo-rig
product ......
p. 607. The equilibrium for 6.219 must include a COOH unit,
not a COOMe unit.
p. 610. First paragraph - line 7. Change 6.246 to 6.247
- line 9. Change 6.266 to 6.246
The structure in the last reaction sequence on the bottom of the
page should be labeled 6.248 and not 2.646.
p. 613. The first line is redundant to the bottom line on p. 612.
Delete the first line on p. 613.
p. 632. Last paragraph - line 3. Change 7.1 to 7.5
p. 636. Last paragraph - line 3. Change 7.46 to 7.48
p. 644. First paragraph - line 2. A Si is missing. It should read
....and 2-(trimethylsilyl)ethoxymethyl chloride
(Me3SiCH2CH2OCH2Cl) generates the .....
p. 663. Structure 7.163 should be a tosyl-ester. The structure should be -
p. 724. Top of the page - continuing paragraph. The second sentence
should be changed from
....a dramatic decrease in metal-halogen exchange, to
....a dramatic decrease in formation of the organolithium reagent,
Note - not in text - in 2nd paragraph. Bailey's reaction as described in this
example (see 8.227) only works well with primary iodides.
p. 740. (**) Table 8.18. 3rd row, 7th entry. change to Ph3C-H
p. 751. Entry 3 in Table 8.19. For 8.386, change + into -.
It should be -
p. 754. First paragraph - line 1. Change 8.434 to 8.405
First paragraph - line 8. Change 8.434 to 8.405
Second paragraph - line 6. Change 2-bromopropionate
to 3-bromopropanoate
Structure 8.409 is missing a methyl group. It should be -
p. 762. First paragraph - line 6. nitrogen is misspelled.
p. 763. In Table 8.21. The item in the table marked % 8.488
should be - % 8.463
p. 768. The stereochemistry of the vinyl group in 8.499 is incorrect.
It should be -
p. 797. First paragraph - line 5. Change 8.657 to 8.675
p. 807. The cyclopropyl group in 8.757 should be on the other
five-membered ring. The structure should be -
p. 812. Structure 8.783 is incorrect. It should be -
p. 815. For the reaction of 8.807, the ketone moiety reacts. Note that in
the absence of the ketone, esters can also react with this reagent,
as seen in the reactions of 8.798 and 8.800.
p. 829. REFERENCE. Under 3. Spelling. Wšhler, F.
p. 877. Last paragraph - last line. The 'in-line' structure for
HMPA is incorrect. It should be (Me2N)3P=O
p. 886. The bond to the methyl group in 9.116 is missing and the C=O
unit shown should be a single bond (C-O). This structure should be -
p. 887. Second paragraph - line 4. Change 9.130 to 9.122
Structure 9.116 is also incorrect here, as on previous page.
Change it to that shown above for page 886.
Second paragraph - line 7. Change cyclopentane to
cyclopentanone
p. 888. First line - change 9.130 to 9.122
p. 896. Line 9. Change 9.189 to 9.185
p. 897. In the decarboxylation of 9.192 to give 9.193. Change Li - over
the arrow - to LiI
p. 912. First paragraph. Line 2. Change 9.308 to 9.293
Line 3. Change 9.308 to 9.293
Line 4. Change 9.309 to 9.294
p. 925. The label under 9.365 is not syni aldol. It should be syn aldol
p. 930. First paragraph. Line 4. Change 9.395 to 9.396
Second paragraph. Line 14. Change 9.402 to 9.400
p. 931. Structure 9.402 is missing a bond for the carbonyl. It should be
p. 939. For the reaction of 9.451, a note of clarification.
The achiral ketone reacts with the chiral, nonracemic base
(9.451) to form an enolate that is coordinated in a chiral
complex. Reaction of benzaldehyde with this chiral complex
leads to asymmetric induction in the final product.
p. 944. Change the number of strucutre 9.484 to 9.483
Change the number of structure 9.483 to 9.484
p. 945. Change the number of structure 9.482 to 9.487
p. 948. Second paragraph. Line 10. Change 9.610b to 9.510b
Line 17. Change (9.513). to (9.512).
Structure 9.514 is incorrect. It should be
p. 954. First paragraph - line 2. Change 9.551 to 9.550
p. 959. In structure 9.583, delete the -SiEt3. This structure should be
p. 962. Second paragraph. Line 3. Change ethyl bromoacetate
to ethyl bromopropanoate
p. 963. The top two structures are labeled 9.603 and 9.604. Change these
numbers to 9.602 and 9.603.
p. 981. 1st paragraph, 3rd line. It is not ...resperine (10.8) -
It should be ...reserpine (10.8)
p. 983. Last paragraph - line 7. Change last word "in" to "to".
It should read
......forms will be used to address .....
p. 989. Line 9. Change (10.29) to (10.27)
p. 993. Structure 10.32 is incorrect. It should be -
Last paragraph - line 4. Change 4-bromoacetaldehyde
to 4-bromopropanol
p. 995. First paragraph - lines 1,2. The bonds are labeled with numbers
and they should be labeled with letters. Change 1,3,5,7,22,21
to b,d,l,n,w,k. It should read
.....shows that bonds b, d, l, n, w, and k were disconnected.
p. 1000. The structure labeled 10.63 on the left of the diagram is
1,3-butadiene. This compound should be labeled as 10.60
Structure 10.61 is incorrect - it should be conjugated.
The structure should be
p. 1001. First paragraph - line 5. Change introduced to introduction.
It should read
....general method for introduction of the ......
For the longifolene synthesis, conversion of the third
compound to the fourth compound has a reaction arrow with three
steps. A fourth step should be added - 4. 2N HCl, EtOH, 100¡C
p. 1011. Line 4 - the 10.5.A.iii. heading. Change STRONG
into STRING
p. 1015. Paragraph 10.5.B.v. - line 16. Change 9.88 to 10.88
p. 1018. Under reaction 9, the sila-acyloin cyclization. The di-ester has
too few carbons. The reaction should be -
p. 1019. Under reaction 12. The product is missing a methyl group. The
reaction should be -
Under reaction 13, the starting material is incorrect. The reaction
should be -
Under reaction 15, the "middle" ring in the product is also
aromatic. The reaction should be -
p. 1022. Second paragraph. Line 3. Change 10.96 to 10.95
p. 1023. Structures 10.100, 10.101, 10.102 and 10.103 have one too
many carbons in the 'left' chain, and 10.103 is missing a carbon
between the ketone moiety and the first C=C. This sequence
should be -
Last paragraph. Line 12. Change .......tosylate 10.101....
to ....alcohol 10.101.......
p. 1027. Strucure 10.126 at the top of the page should be labeled 10.125
p. 1028. The column of * under RULE should be under 1.
First paragraph. Line 2. Use lower case i rather than I.
It should be i not I
p. 1029. Under 2. The extra filled black dot should not be there.
Under 4. The carbonyl carbon is not the bridgehead carbon.
It should be -
Under 6. The 7s in the table opposite "Rule 2b" should be deleted.
p. 1032. Second paragraph. Line 5. Change 10.150 to 10.149
Line 6. Change 10.149 to 10.150
p. 1033. The structure of vernolepin (10.155) is missing an OH at C-8.
It should be -
This correction should also be made on pp. 1034, 1035, and 1036 -
in Figure 10.11, Figure 10.12, Figure 10.13, and Figure 10.14.
p. 1034. Structure 10.156 in Figure 10.11 should have two lactone rings.
It is missing one carbonyl. It should be -
p. 1035. Structure 10.169 is missing a carbon. It should be -
Last paragraph - line 6. Change then to than. It should read
.....for cleavage of bond 5 than those observed ......
p. 1037. Add labels A, B, C to structure 10.12. It should be
p. 1038. Last paragraph. Line 4. Change dissects
to modifies
p. 1039. The label 10.191 is misplaced. The 10.191 should be under the
imidazolone starting material (the last structure in the
disconnection scheme shown in Figure 10.16).
p. 1040. Second paragraph. Line 9. Change Ref. 124 to 127.
It should read routes.127
Line 12. change 25-step to 25-disconnection
p. 1043. First paragraph. Line 9. Change , r = 1,
to , r = 0,
Line 10. Change = 6+4-0-1 = 10.
to =6+4-0-1 = 9.
p. 1045. First paragraph. First line. Change In to If
p. 1046. Numbers for last term in expression for W.
Change from (5)(20) to (5)(2)
p. 1056. The disconnection in Figure 10.23 with Me-C6H4CHO. The partner
should be an aldehyde, not a ketone. This disconnection pair
should be
p. 1059. Line 7. Change from Generation of cation 10.211 was
to Generation of a cation from 10.211 was
p. 1061. Structures 10.220 and 10.221 are missing an alkene unit.
They should be
p. 1063. First paragraph. Line 3. Change 10.250 to 10.226
p. 1071. Structure 10.274 has the wrong number. It should be labeled 10.269
p. 1076. First paragraph. Line 3. Change 10.306 to 10.281
p. 1096. Problem 10 (c) - top of the page. The name of this compound is
ophiobolin F
p. 1101. Last paragraph - line 12. Add "is" after which. It should read
.....predict which is the higher and which is the lower energy transition .......
p. 1108. The coefficients for the HOMO of 11.9 and 11.11 are reversed.
They should be -
First paragraph - lines 1,2. Change this sentence to read
....In the HOMO the orbital on the carbon distal to Z attached to C-1
is largest for the HOMO and smallest for the LUMO (see 11.9).
This is reversed when Z is attached to C-2 (see 11.10).
p. 1111. In Figure 11.6, the [2+2]-cycloaddition is a HOMO-HOMO
interaction and the diagram must be changed. It should be -
p. 1113. In Figure 11.7, the LUMO of the alkene is incorrectly shaded.
It should be -
p. 1116. First paragraph - line 2. Change Fig. 11.8 to Fig. 11.9
p. 1126. For the transition model 11.88, add dotted lines to denote bond
formation. It should be -
p. 1127. See new structures 11.90 and 11.92 to clarify positions of bond
formation and stereochemistry. These should be -
p. 1132. Structure 11.112 should be a dimethylalkylidene, not a
cyclohexylidene. It should be -
p. 1147. Second paragraph - line 4. Change (11.1800 to (11.180)
p. 1149. Last paragraph - line 1. framework is one word, not two.
pp. 1151-1152. Note position change in 11.218 to make it clearer how
the cycloaddition product forms. In addition, 11.215 was "flipped"
to make it clearer how that product formed. This sequence should be -
p. 1158. At the bottom of the page, the structure labeled 11.262
should be 11.261
Note - Structures 11.262, 11.263 and 11.264 are all in equilibrium.
Likewise, 11.269, 11.270, and 11.271 are all in equilibrium.
The equilibrium arrows were not put in as they should have been.
p. 1181. Structure 11.397 is missing an oxygen. It should be -
p. 1182. The undefined stereocenter in 11.399 should be as shown in this
new structure.
p. 1187. Structure 11.435 has an extra methyl group. It should be -
Connect the bonds in 11.427
p. 1198. NOTE - not in text.. For the reaction of 11.455 and 11.456, the selectivity
(mentioned in the last paragraph) is due to the fact that both
alkene reactants are confined to a ring. A cyclohexenone
derivative and butene give a mixture of diastereomers.
p. 1221. In structure 11.601, the N-benzyl structure is incorrect.
It should be a benzyl amide. The structure should be -
In structure 11.606, a OMe group is missing. Note that the
OMe group eliminates to form the iminium moiety that undergoes
cycloaddition. The structure of 11.606 should be -
p. 1230. The transition state 11.664 is misleading as to which bonds are
formed. A better representation is -
p. 1237. NOTE - not in text.For the rearrangement of 11.715, it is argued that 11.716 is not
an intermediate and that a [5,5]-sigmatropic rearrangement leads
directly to 11.717 (see Tetrahedron Lett., 1985, 26 4319.)
p. 1242. Structure 11.748 is missing an oxygen. It should be an ester,
not a ketone. The structure should be -
p. 1246. Paragraph 11.12.D.iii. - line 6. Change aza-Claisen to
thio-Claisen
Structure labeled 11.724 near the bottom should be 11.723
p. 1247. The structure 11.793 is incorrect. It should be -
p. 1248. Last paragraph. Change 11.758053 to 11.805
p. 1249. NOTE. See Chem. Ber., 1977, 110, 3624
Structure 11.806 is incorrect. It should be
p. 1250. At the bottom of the page the reaction that gives 11.809 shows
an arrow going to H. That arrow should go to carbon. It should be -
p. 1257. Structure 11.852 is incorrect. It should be -CH2OH and not -OH.
It should be -
p. 1258. Line 11 - Change % de to % ee. It should be
.....of 11.863 (98% ee). The titanium ......
p. 1281. Add a positive charge (+) to the N2 unit of 12.7.
p. 1290. Structure 12.25 should have a positive charge (+) near the
"bridging" hydrogen atom.
p. 1294. The path a/path b labels are reversed. The reaction of 12.51 to
give 12.54 should be path a. The reaction of 12.51 to give
12.52 should be path b.
p. 1295. Structure 12.57 is missing a positive charge. It should be -
p. 1301. Last paragraph. Line 10. Change (12.107) to (12.100)
p. 1304. The last disconnection at the bottom of the page. The polyene has a
double bond out of place. That structure should be
p. 1309. First paragraph. Last line. change (12.238).
to (12.156).
p. 1338. The AsO5 reagent under the reaction arrow for the 12.291
to 12.292 transformation should be As2O5 or As4O10.
paragraph 1, line 3. change line as follows.
.....(12.289) in situ. Cyclization and air oxidation under Friedel-Crafts.....
p. 1342. Line 11. Change 12.337 to 12.317
p. 1343. First line. Change (see 12.339) to (see 12.324)
p. 1345. Line 6. Change 12.337 to 12.336
p. 1347. One aromatic ring in 12.344 is not aromatic. It should be -
p. 1351. Line 11. Change 12.370 to 12.363
p. 1352. The reaction arrow should go from 12.372 to 12.371.
It should be -
p. 1353. First paragraph - line 5. Change "Ph - H" to "Pd - H"
Structure 12.379 should be a pi-complex, not as shown.
It should be -
p. 1354. "Under" the reaction arrow (12.382 to 12.383) - Not P Ph3
it should be PPh3
p. 1356. In Table 12.18 - the structure numbers should be changed.
Change from % 12.390 and % 12.391 to
% 12.389 and % 12.390
p. 1358. Structure 12.408 is incorrect. It should be
p. 1359. First line. Change "dbu" to "dba" in both cases.
p. 1365. Paragraph after 12.6 - line 2. Change nitrogen to nickel.
It should read
....is the nickel analog of ......
p. 1373. Last paragraph - line 1. Spelling. allyltin not allylin
pp. 1372-1373. NOTE - not in text.In a personal communication, Professor H.M.R. Hoffmann
(Hannover) points out that intermediates such as 12.498 and 12.502
are probably not anionic as illustrated, but rather cations bound to a
metal, and probably look like -
He points out other synthetic applications in J. Am. Chem. Soc., 1972,
94, 3201; J. Am. Chem. Soc., 1972, 94, 1373, 3201, 3940, 6213,
7832; Angew. Chem. Int. Ed. Engl., 1973, 12, 239.
He also points out that the reagent Zn/B(OEt)3 is a less toxic and less
expensive alternative to Fe2(CO)9 - see Tetrahedron Lett., 1975, 4487.
p. 1375. "Middle" paragraph. Line 2. Change 3-methyl-1-bromo-1-butene
to 3-methyl-1-bromo-2-butene
Line 5. Change 12.522 to 12.517
p. 1376. Reagent 12.524 (under the reaction arrow) is a silane.
Its structure is CH2=CHCH2-SiMe3.
Structure 12.522 has the incorrect stereochemistry. It should be
p. 1412. Over the arrow for the reaction of 13.67 to give 13.68,
change PhCH2CH3 to PhCH=CH2
p. 1421. Last line. change 13.142 to 13.145
p. 1451. Structures 13.306 (should be C-triple bond-N) and 13.1309
(last structure has N-H not N-N) are incorrect. They should be -
p. 1454. Structure 13.328 is incorrect. It should be
p. 1459. The last disconnection. Change n+1 to n. It should be
p. 1491. HOMEWORK. Problem 16 (k). Spelling. Liebigs