Page 1194 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

regioselectivity of, 844–848 diisopinocampheylborane 1181
frontier MO analysis of, 844–847 in enantioselective reduction of ketones, 194
stereochemistry of, 839 hydroboration by, 529–531 Index
Alder rule for, 840–841 dimethoxymethane
computational analysis of, 852–853 conformation, 83
Lewis acids, effect on, 853 stabilization of, 262–263
secondary orbital interactions in, 842, 854–855 dimethyl sulfoxide
substituent effects on, 843–848 as solvent, 363, 411–412
synthetic applications of, 860–864
2,4-dinitrofluorobenzene
transition structures for, 840–841
nucleophilic substitution reactions of, 820
aromaticity of, 851
dinitrogen, see Nitrogen, molecular
charge transfer character in, 847, 857–858,
DIOP, see phosphines
950
dioxoles
computational characterization of, 851–860
anomeric effects in, 233
synchronicity of, 852, 855–856
DIPAMP, see phosphines
water, as solvent for, 850
1,2-diphenylethane-1,2-diamine
1,4-dienes
as chiral shift additive for NMR, 210
photochemical reactions of, 1112–1116
diphenylpicrylhydrazyl, as radical inhibitor, 994
1,5-dienes
1,3-dipolar cycloaddition reactions, 873–888
[3,3]-sigmatropic rerrangements of, 920–930
application of DFT concepts to, 950–951
substituted, BDE for, table, 988
Bell-Evans-Polyani relation in, 883
dienes, see also specific dienes e.g. 1,3-butadiene
addition reactions catalysis of, 886–888
bromination of, 496–497 computational modeling of, 887
with hydrogen halides, 481 tris-aryloxyaluminum as, 886
conformation of, 149–151 comparison with Diels-Alder reaction, 883
in Diels-Alder reactions, 842 computational model of, 880–883
Danishefsky’s diene, 864 examples of, 885
in Diels-Alder reactions, 839 frontier MO interpretation of, 874–882
2-substituted, 847–848 intramolecular, 884
effect of conformation, 842 regiochemistry, 880–883
effect of substituents on rate, 842–848 effect of catalysts, 886–888
electrocyclic reactions of, 892–893 electronic versus steric control, 880, 886
global electrophilicity of, table, 946 stereochemistry of, 877–879
local electrophilicity of, 947 synchronicity of, 882
local nucleophilicity of, 947 synthetic pplications of, 884–886
local softness of, 948 1,3-dipoles
photochemical reactions of, 1100–1104
characteristics of, 874
computational interpretation, 1137–1145
examples of, 875
photoisomerization of, 1096–7
frontier orbitals of, 880–881
quinodimethanes as, 857, 864
global electrophilicity of, 950
dienophiles, 839
dipolarophiles
chiral acrylate esters as, 865–866
frontier orbitals of, 845–847
effect of substituents on reactivity, 843–848
relative reactivity of, table, 876
examples of, 844
with ethene, 883
frontier orbitals of, 846–847
dipole moment
global electrophilicity of, 946
computation of, 53
local electrophilicity of, 947
diradicals
local nucleophilicity of, 947
photochemical generation, 1123
local softness of, 948
structural effect on lifetimes, 1017–1018
nitroethene as, 862
quinones as, 862 disiamylborane
vinylphosphonium salts as, 863 formation of, 188
vinyl sulfones as, 863 hydroboration by, 524
vinyl sulfoxides as, 863 dispersion forces, 24
dihydroxylation of alkenes disrotatory, definition, 893
enantioselective, 200–203 dithianes
computational model for, 202–203 acidity of, 599
reagent control of, 206–207 anomeric effects in, 233