Subject Index
A
absolute temperature 227
acetate 249
acetolysis 231ff, 269, 271, 273ff
acetonitrile 190, 212
acetophenone 15
acetoxonium ion 164
– intermediate 164
acetoxy group 164
(2-acetoxyvinyl)iodonium bromide, Z- Z Z
203, 205f, 209
acid-base catalyzed reactions 71
acid-base exchange 219
acid catalysis 71, 154f
– formation of an oxacarbenium ion
89
– hydrolysis of glycopyranosides 87
– hydrolysis of methyl 5-thioxylopyranosides 89
– hydrolysis of methyl
xylopyranosides 88
– isomerization of imines 177
– process 154
acid methanolysis of (+)-styrene oxide
70
acid solvolysis 73
activated complex 117, 212, 216, 228f
activating groups 169
activation
– energy 226f
– entropy 228
– of carboxylic acids 174
– parameters 113ff, 225ff
acyclic 2-azadienes 119
acyl-6-amino-3-(methylthio)-1,2,4,5tetrazines, N- 197
N N
acyl ammonium salt 63, 65
acyl aziridines, 2- 203, 209
acyl iminium ion 188
acylium ion 63
acyl-1,2,4,5-tetrazines, N- 197
addition 171
–, concerted 51f
–, conjugate 213
–, 1,4-(conjugated)hydride 40
–, electrophilic 18, 30
– -elimination 251, 253
– mechanism 254, 256
– pathway 256
– process 154, 157, 205, 257
– route 256
– sequence 217
– S N Ar mechanism 174
–, 1,2-hydride 40
–, Michael-type 160
– of hydroxylamines 47
adduct, [4+2] 198
adduct, V 238f
adduct, endo 104
aliphatic bimolecular nucleophilic
mechanism (S N 2) 90, 233
alkenes 145
alkyl shift 275
alkylating agents 11
alkylation of aromatic nitro compounds
237
alkylation of indole 11
alkylhydroxylamines, N- and
N N
O- 49
alkylphthalimides, N- 108
N N
alkylsilane 111
alkyne-allene base-catalyzed
isomerization 161
alkynyl cyclobutenone 159
allene 45
allyl ether 39f
allylic 1,3-strain 150
allylstannanes 18
allyltributylstannane 14, 18
amide radicals 262
amidyl radical 259
amine 68
– -catalyzed reaction 64
–, pK a values 114
a
amino alcohols 34, 36
aminobenzoate, 2- 154
–, esters 153
aminolysis 115, 117f
– of 4-nitrophenyl N-benzylsulfamate
113
– reactions 114
ammonium hydroxide 131
ammonium salt 63, 175
anilides 259, 265
anion translocation 186, 188
A
absolute temperature 227
acetate 249
acetolysis 231ff, 269, 271, 273ff
acetonitrile 190, 212
acetophenone 15
acetoxonium ion 164
– intermediate 164
acetoxy group 164
(2-acetoxyvinyl)iodonium bromide, Z- Z Z
203, 205f, 209
acid-base catalyzed reactions 71
acid-base exchange 219
acid catalysis 71, 154f
– formation of an oxacarbenium ion
89
– hydrolysis of glycopyranosides 87
– hydrolysis of methyl 5-thioxylopyranosides 89
– hydrolysis of methyl
xylopyranosides 88
– isomerization of imines 177
– process 154
acid methanolysis of (+)-styrene oxide
70
acid solvolysis 73
activated complex 117, 212, 216, 228f
activating groups 169
activation
– energy 226f
– entropy 228
– of carboxylic acids 174
– parameters 113ff, 225ff
acyclic 2-azadienes 119
acyl-6-amino-3-(methylthio)-1,2,4,5tetrazines, N- 197
N N
acyl ammonium salt 63, 65
acyl aziridines, 2- 203, 209
acyl iminium ion 188
acylium ion 63
acyl-1,2,4,5-tetrazines, N- 197
addition 171
–, concerted 51f
–, conjugate 213
–, 1,4-(conjugated)hydride 40
–, electrophilic 18, 30
– -elimination 251, 253
– mechanism 254, 256
– pathway 256
– process 154, 157, 205, 257
– route 256
– sequence 217
– S N Ar mechanism 174
–, 1,2-hydride 40
–, Michael-type 160
– of hydroxylamines 47
adduct, [4+2] 198
adduct, V 238f
adduct, endo 104
aliphatic bimolecular nucleophilic
mechanism (S N 2) 90, 233
alkenes 145
alkyl shift 275
alkylating agents 11
alkylation of aromatic nitro compounds
237
alkylation of indole 11
alkylhydroxylamines, N- and
N N
O- 49
alkylphthalimides, N- 108
N N
alkylsilane 111
alkyne-allene base-catalyzed
isomerization 161
alkynyl cyclobutenone 159
allene 45
allyl ether 39f
allylic 1,3-strain 150
allylstannanes 18
allyltributylstannane 14, 18
amide radicals 262
amidyl radical 259
amine 68
– -catalyzed reaction 64
–, pK a values 114
a
amino alcohols 34, 36
aminobenzoate, 2- 154
–, esters 153
aminolysis 115, 117f
– of 4-nitrophenyl N-benzylsulfamate
113
– reactions 114
ammonium hydroxide 131
ammonium salt 63, 175
anilides 259, 265
anion translocation 186, 188