Page 1192 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

chair versus boat transition structure for, 923 destabilization of, 718, 726 1179
computational modeling of, 926–927 generation of, 725
cyano substitutents, effect on, 927 Huckel MO diagram for, 714 Index
of divinylcyclopropane, 929 reactions of, 725
effect of strain on, 928 structure of, 726
More-O’Ferrall-Jencks diagram for, 928 1,3-cyclohexadiene derivatives
of semibullvalene, 931 electrocyclic ring opening of, 1108–1109
stereochemistry of, 922–923 photoproducts from, 1106, 1112
substituent effects on, 924–928 cyclobutane derivatives
covalent radii, 24 conformation of, 162
definition within DFT, 97 formation by cycloaddition, 891
table of, 25, 98 cyclobutenes
Crabtree catalyst, 174 1-aryl
cracking, 454–456 photoproducts from, 1105
Cram’s rule, 179 electrocyclic ring opening of, 892–893
critical micellar concentration, definition, 219 3,4-dichlorocyclobutene, 903
critical point, in electron density distribution, 63 inward versus outward rotation during,
for substituted methanes, 66–68 901–903
crown ether catalysts, 364–365 stereochemistry of, 896–897
CSP, see chiral statinary phase photochemical reactions of, 1104–1105
cubane cyclodecane
acidity of, 373–374 conformation of, 165–166
halogenation of, 1003 cycloheptane
Curtin-Hammett principle, 296–297 conformation of, 163–164
cyano groups cycloheptatrienes
anion stabilization by, 598 electrocyclic reactions of, 905
cyanohydrins sigmatropic shift of hydrogen in, 917–918
formation from carbonyl compounds, 635 cycloheptatrienyl cation
cycloaddition reactions, 834–892 aromaticity of, 32, 740
[2+2] of ketenes, 835, 888–892 cycloheptene
azetidinones from, 891–892 photoreactions of, 1094
intramolecular, 890–891 1,5-cyclohexadienone
orbital array for, 888–889 4,4-diphenyl, photochemistry of, 1130–1132
stereoselectivity of, 890 cyclohexane derivatives
transition structure for, 889 alkyl, conformation of, 157–159
1,3–dipolar cycloaddition as, see also 1,3-dipolar chloro-
cycloaddition, 834 conformational half-life of, 153–154
antarafacial and suprafacial modes of, 836 conformation of, 152–161
application of DFT concepts to regiochemistry, iodo- conformation by NMR, 156–157
945–951 kinetics of ring inversion, 152–156
Diels-Alder as, see also Diels-Alder reaction, cyclohexanone derivatives
834 conformation of, 161
as examples of concerted pericyclic reactions, stereoselective reduction of, 176–179
834 cyclohexene
Huckel versus Mobius topology of, 836 1-phenyl
of ozone with ethene, 49–50 photodimerization of, 1110–1111
photochemical, of alkenes, 1125–1126 conformation of, 170
Woodward-Hoffmann rules for, 836–837 photoreactions of, 1094–1095, 1110
cycloalkanes cyclohexyl radical
configuration of, 121 structure of, 984
conformation of, 161–166 1,3-cyclooctadiene
molecular symmetry of, 133 photocyclization of, 1101
strain in, 161–166 1,4-cyclooctadiene
cycloalkenes photocyclization of, 1111
chirality of, 130 1,5-cyclooctadiene
E-cycloalkenes, racemization of, 131 photochemistry of, 1145
photochemistry of, 1094–1096 cyclooctane
1,3-cyclobutadiene conformation of, 164–165
antiaromaticity of, 714, 718, 726 cyclooctatrienyl cation, 743