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p. xxxvii. abbreviations
CAN (NH)2Ce(NO3)6 should be (NH4)2Ce(NO3)6
p. xxxviii. abbreviations
DABCO 1,4-Diazobicylco[2.2.2]octane should be 1,4-Diazabicylco[2.2.2]octane
DCC C6H13-N=C=N-C6H13 should be C6H11-N=C=N-C6H11
Diphos 1,2-bis-Diphenylphosphino)ethane should be 1,2-bis-(Diphenylphosphino)ethane
Diphos-4 1,4-bis-Diphenylphosphino)butane should be 1,4-bis-(Diphenylphosphino)butane
p. xxxix. abbreviations
EE 1-Ethoxyethyl should be 1-Ethoxyethoxy
and
EtO(Me)HCO should be EtO(Me)CH
HMPA (Me3N)3P=O should be (Me2N)3P=O
HMPT (Me3N)3P should be (Me2N)3P
p. xl. abbreviations
Pip Piperidinyl should be Piperidino
p. xli. abbreviations
TEBA Bn(Me)3N+ should be Bn(Et)3N+
Ts(Tos) 4-MeC6H4 should be 4-MeC6H4SO2
chapter 1, p 10. Remove double period
( C-C-Br to C=C ). In the actual synthesis, the required reaction is the reverse of
this retroreaction. It is also possible to write a functional group exchange based on
the alkene as C=C to C-C-Br.
chapter 2. p 75. interchange right and left. It should be
A consequence of this trend in acidity is that basicity increases from right to left across the periodic table.
chapter 4. p 358
(1st paragraph)
called the Felkin-Anh model.279 When RM is small relative to RS, there is little difference in the destabilizing
(2nd paragraph)
The Felkin-Anh and Cram models are best applied to acyclic systems. Problems arise when any of these
(3rd paragraph)
Cram selectivity, possibly due to "destabilization of the minor Felkin-Anh transition state (283) as a result of
chapter 4. p 359
(last paragraph)
leading to formation of 287. As seen in 286, the Felkin-Anh model easily accommodates a chelated
chapter 4. p 362
(2nd paragraph)
results. The Felkin-Anh model suggests an interaction such as that shown in 297.291 An alternative proposal
(last paragraph)
molecule into that chair conformation (sec. 1.5.D). An attempt to use the Cram model or the Felkin-Anh
chapter 4. p 366. Numbers for ketones are incorrect - see changes
Table 4.13. Selectivity in Hydride Reduction of Bicyclic Ketones
Bicyclic Ketone Reagent % ax Alcoholb % eq Alcohola
319 NaBH4 15 85
LiAlH4 13 88
320 NaBH4 11 89
LiAlH4 10 90
321 NaBH4 6 94
LiAlH4 6 94
322 NaBH4 40 60
323 NaBH4 72 28
chapter 4. p 432. References. add reference (c)
279 (a) Chrest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett., 1968, 2199; (b) Chrest, M.; Felkin, H. (i>Tetrahedron Lett.,
1968, 2205; (c) Anh, N.T.; Eisenstein, O. Nov. J. Chem., 1977, 1, 61.
chaper 5, p 482. change endo products 199 and 200 to exo products.
chapter 5, p 484. change structure of O-hydroxyamine 212
chapter 5, p 491. Add (a) and (b) to the 2 references in ref 145
145 (a) Brown, H.C.; Rogic, M.M.; Rathke, M.W.; Kabalka, G.W.
J. Am. Chem. Soc, 1968, 90, 818,
(b) 1911.
chapter 6. p 517. caption over arrow (161 - 162) exo-yet should be exo tet
chapter 8. p. 692. Anh is mispelled
4. In each case, draw the transition state for the Cram, Karabatsos and Felkin-Anh models of the reaction of
chapter 9. p 729. Structure 49 should be changed to a cyclohexanone
chapter 9. p 776 Anh is misspelled
deprotonation, using the Felkin-Anh model (sec. 4.7.B). Conformation 402 is more stable than 403 for
Chapter 10. p 834. transpose carbonyl
in Scheme 10.4. Corey's synthesis of longifolene (73).
chapter 10. p 872. change temples to templates
in Figure 10.13. Hidden chiral templates.
chapter 11, p 943. change ,. to , after pathway
dropped to 3.1% upon heating at 50 degrees C for 60 min,102 which is consistent with a
reversible reaction pathway, favoring the more stable exo product.102 This reverse reaction
(cycloadduct to diene + dienophile) is called a retro Diels-Alder reaction.103
chapter 11. p 1026 under base - list line "none" - 2nd line 2.2 equiv KH
Table 11.23. Acceleration of the Claisen Rearrangement by Sulfoxide Stabilized Anions
Base Solvent Temp., degreesC Time, h 632/633 Yield (%)
none DMSO 100 4 96:4 97
2.2 equiv KH DMSO 20 4 93:7 79
THF 20 4 89:11 78
chapter 11. p 1033 add methyl groups
chapter 12. p 1128 Anh is misspelled
increased, the diastereofacial selectivity increased for the syn diastereomer relative to allyltin compounds. In
the example cited, the chelation product exceeded the product predicted by the Felkin-Anh model (sec.
4.7.B), being formed in a ratio of >200:1. In general, the Felkin-Anh model (predicting the syn diastereomer)
chapter 13. p 1151 change energy values
cleavage. Dissociation of C-C (85 kcal mol-1; 357 kJ mol-1)18, C-O (84 kcal mol-1; 351 kJ mol-1),18
H-O (111 kcal mol-1; 464 kJ mol-1),18 and Chalogen bonds (55 kcal mol-1 for C-I to 79.8 kcal mol-1 for
C-Cl; 230 kJ mol-1 to 351 kJ mol-1)18 all require high reaction temperatures for homolytic
chapter 13. p 1153 change energy values
provided by IR, visible or UV light. An energy of 10 kcal mol-1 (42 kJ mol-1) corresponds to 3500 cm-1,
which is in the IR. Light of wavelength 2000 corresponds to 143 kcal mol-1 (598 kJ mol-1), and is at the
lower end of the ultraviolet (UV) region. Light in the UV or visible region can excite molecules to higher
electronic states. Wavelengths in the UV are usually expressed in nanometers (1 nm = 1 mm = 1 x 10-7 cm)
and a wavelength of 200-400 nm is used most often for inducing photolysis in the UV region for common
functional groups (sec. 11.10.B).
chapter 13, p 1183. Change 220 to a quinone radical rather than a phenol radical.
chapter 13, p 1229. Add reference (b) to ref 152.
152 (a) Barton, D.H.R.; Deflorin, A.M.; Edward, O.E. J. Chem. Soc., 1956, 530;
(b) Scott, A.I. Quart. Red., 1965, 19, 1.
General Index. Anh is mispelled
Felkin-Anh model 692
General Index. p 1348. Leis should be Lewis
substitution, aromatic, electrophilic 156-165, 1080
+I and -I effects 160-161
+M and -M effects 160-161
activating and deactivating
groups 1080
and heterocyclic rings 159-160
and Lewis acids 157
Named Reaction Index. Anh is mispelled
Felkin-Anh model 358, 692, 776-777, 1128
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