Subject Index 279
C
camphor-derived oxazoline N-oxides N N
101
canonical form 181, 267, 275
carbamate intermediate 132
carbanion 205, 237f, 240
– intermediates 81, 255f
carbenium ion 87, 90, 95
carbocation 27, 30, 55, 59, 72f, 76f, 91,
99, 100, 170, 194
–, E- 18
carbon-centered radical 259, 266
carbonium ion 92
carbonyl group 22
carbonyl oxygen atom 16
carbonyl ylides 140
carboxylic acid 131, 137, 169
carboxymethylating reagent 135
cascade cyclization 161
cascade electrocyclic ring closures 162
cascade electrocyclic ring opening 162
cascade radical cyclization 267
catalysis 63, 69, 211ff
–, acid 71, 155
–, general 116f
–, general-base 79, 83
catalyzed decomposition of diazo esters
144
catalyzed E1cB mechanism 118
catalyzed process 220
cation 93
– -solvating solvent 188
– solvator 207, 257
cationic intermediate 81
cationic mechanism 100
C-C V bond assistance 272
CDMT 169
CeCl 3 24f
CF 3 SO 3 H 97
13 CH 3 I 133
C-H insertions 140
change in the rate-determining step 117,
237f
– in an E1cB mechanism 113
charge development 75
charge-separated diradical 108ff
chelate-controlled carbonyl addition
reactions 125
chelated transition states 128
chelating ability 23
chelating agent 128
chelation 43
13 C chemical shifts 165
chemoselectivity 14
chiral 225
– center 22
chlorine KIE 170, 173
chloro-4,6-dimethoxy-1,3,5-triazine, 2169
chlorohydrins 27
chloropropionate, 2- 242
chloro-1,3,5-triazines, 2- 169, 174
chromium Fischer alkoxy carbene
complex 39
cinnamate 47–52
– E- 47
classical carbocation 57, 60, 274
– intermediate 273
coefficients 201
– of the atomic orbitals 103f, 199
competing reaction pathways 3, 27
competitive pathways 6
complex reaction 220
complex, activated 117, 212, 216, 228f
concerted addition 51f
concerted mechanism 47, 51, 169, 251
concerted perpendicular attack 256
concerted process 27, 84
concerted syn-elimination 192f
concerted transition state 30
concerted versus stepwise mechanism
251
condensation 6
configuration, retained 253
conformational change 225
conformations 23
conformers 255
conjugate addition 213
conjugation 181
conrotatory electrocyclization 98
conrotatory six-electron ring closure 99
conrotatory transition state 98
consecutive reaction 175
coordinating solvents 24
Cope eliminations, retro- 51
correlation coefficients 141
Cram’s cyclic model 23, 130
Cram’s model 128
crossover 30, 31
– experiments 27, 30ff, 188
cross-products 30
crowded conformation 193
C
camphor-derived oxazoline N-oxides N N
101
canonical form 181, 267, 275
carbamate intermediate 132
carbanion 205, 237f, 240
– intermediates 81, 255f
carbenium ion 87, 90, 95
carbocation 27, 30, 55, 59, 72f, 76f, 91,
99, 100, 170, 194
–, E- 18
carbon-centered radical 259, 266
carbonium ion 92
carbonyl group 22
carbonyl oxygen atom 16
carbonyl ylides 140
carboxylic acid 131, 137, 169
carboxymethylating reagent 135
cascade cyclization 161
cascade electrocyclic ring closures 162
cascade electrocyclic ring opening 162
cascade radical cyclization 267
catalysis 63, 69, 211ff
–, acid 71, 155
–, general 116f
–, general-base 79, 83
catalyzed decomposition of diazo esters
144
catalyzed E1cB mechanism 118
catalyzed process 220
cation 93
– -solvating solvent 188
– solvator 207, 257
cationic intermediate 81
cationic mechanism 100
C-C V bond assistance 272
CDMT 169
CeCl 3 24f
CF 3 SO 3 H 97
13 CH 3 I 133
C-H insertions 140
change in the rate-determining step 117,
237f
– in an E1cB mechanism 113
charge development 75
charge-separated diradical 108ff
chelate-controlled carbonyl addition
reactions 125
chelated transition states 128
chelating ability 23
chelating agent 128
chelation 43
13 C chemical shifts 165
chemoselectivity 14
chiral 225
– center 22
chlorine KIE 170, 173
chloro-4,6-dimethoxy-1,3,5-triazine, 2169
chlorohydrins 27
chloropropionate, 2- 242
chloro-1,3,5-triazines, 2- 169, 174
chromium Fischer alkoxy carbene
complex 39
cinnamate 47–52
– E- 47
classical carbocation 57, 60, 274
– intermediate 273
coefficients 201
– of the atomic orbitals 103f, 199
competing reaction pathways 3, 27
competitive pathways 6
complex reaction 220
complex, activated 117, 212, 216, 228f
concerted addition 51f
concerted mechanism 47, 51, 169, 251
concerted perpendicular attack 256
concerted process 27, 84
concerted syn-elimination 192f
concerted transition state 30
concerted versus stepwise mechanism
251
condensation 6
configuration, retained 253
conformational change 225
conformations 23
conformers 255
conjugate addition 213
conjugation 181
conrotatory electrocyclization 98
conrotatory six-electron ring closure 99
conrotatory transition state 98
consecutive reaction 175
coordinating solvents 24
Cope eliminations, retro- 51
correlation coefficients 141
Cram’s cyclic model 23, 130
Cram’s model 128
crossover 30, 31
– experiments 27, 30ff, 188
cross-products 30
crowded conformation 193