Page 1207 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

1194 pseudorotation disproportionation, 966
in relation to cyclopentane conformations, 163 group transfer reactions, 1037–1039
Index pyrans halogenation, 1002–1004, 1018–1024
formation by electrocyclization, 910–911 energetics of, 1018–1020
pyridine derivatives selectivity of, 1019–1020
aromaticity of, 758 substituent effects on, 1003–1004
dihydro by electrocyclization, 910–911 hydrogen atom abstraction, 1001–1004
electrophilic aromatic substitution of, 794 inhibitors for, 994–5
nucleophilic aromatic substitution of, 820 initiation, 965
2-pyridone iodine atom transfer, 1037–1038
catalysis of carbohydrate anomerization, 674 kinetics of, 992–995
catalysis of ester aminolysis by, 661–662, propagation, 965
673–674 rates of, 995–1000
pyrrole competition methods for, 995–996
aromatic stabilization of, 758–760 table of, 997–1000
electrophilic aromatic substitution of, 793–794
rearrangement, 1041–1044
of cyclopent-2-enylmethyl radical, 1044
quantum yield, 1077 examples, 1044
quenching, 1077 of hex-5-enoyl radical, 1042–1043
quinodimethanes selenyl group transfer reactions, 1038–1039
as Diels-Alder dienes, 857, 864 Lewis acid catalysis of, 1039
quinoline alkaloids spin trapping of, 973
as chiral shift additives, 210 stereochemistry of, 983–986
DHQ, 200 examples of, 983
DHQD, 200 substitution by S RN 1 processes, 1044–1052
as ligands in alkene dihydroxylation, 200–203 mechanisms for, 1044–1045
of nitro compounds, 1045–1048
racemate, see racemic mixture
termination, 965
racemic mixture
with oxygen, 1023–1026
properties of, 123–124
-scission, 966–7, 1013
racemization radicals, see also alkyl, aryl, vinyl etc.
of allylic sulfoxides, 940
9-decalyloxy
during nucleophilic substitution, 396, 398
fragmentation of, 1016
during radical reactions, 983–984
acyl
of E-cyclooctene, 131
radical anions, 988 decarbonylation of, 967, 1017
from naphthalene, 990 acyloxy
decarboxylation of, 967
in S RN 1 substitution, 1045–1052
alkoxyl
radical cations, 988
formation from alkyl hypochlorites, 1015
radical reactions
addition reactions alkyl
of aldehydes, 1031, 1034 disproportionation, 966
comparison of, by computation, 1007–1008 allyl
examples of, 1033–1036 resonance of, 312–313
of halomethanes, 1029–1031, 1036, 1041 subtituent effects on, 985–987
of hydrogen halides, 1026–1028 bridgehead, 984–985
rates of, 1004–1008 ESR parameters for, 985
substituent effects on, 1004–1006 capto-dative, 316, 987–988
atom transfer, 966 examples, 989
chain length, 965 charged, 988–992
cyclization, 1008–1013 cyclization of unsaturated, 1008–1013,
8-endo cyclization to lactones, 1013–1014 1037–1039
atom and group transfer reactions in, cyclohexyl
1037–1039 structure of, 984
computational modeling, 1010–1012 delocalized, 312–313
rates of, 1008–1013 detection of, 966–976
regiochemistry in relation to ring size, by CIDNP, 974–975
1009–1010 by ESR spectroscopy, 970–971
stereoelectronic effects on, 1009–1010 by spin trapping, 973