Page 1188 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

resonance in, 62 bond length 1175
substituent effects on, 432–433 computation by MO methods, 51
benzyl radical as a criterion of aromaticity, 718–719 Index
resonance in, 312–313 bond order
substituent effects on, 986–987 in carbonyl compounds, 320–321
benzyne as a criterion of aromaticity, 723–724
additions to, 823 of hydrocarbons, 77
generation of, 821–824 relation to electron density, 76–77
biaryls bond path
chirality of, 129–130 AIM definition, 63
bicyclo[1.1.0]butane, 87–88 bonds, see chemical bonds
reaction with halogens, 87 9-borabicyclo[3.3.1]borane
bicyclo[1.1.1]pentane, 87–88 formation of, 188
bicyclo[2.2.0]hexa-2,5-diene hydroboration by, 524, 533
conversion to benzene, transition structures for,
boranes
904
alkyl
derivatives of, 904
chiral, 529–531
kinetic stability of, 904
formation of, 188
synthesis of, 904
halogenation of, 529
bicyclo[4.1.0]hepta-2,4-dienes
hydroboration by, 524
electrocyclic reactions of, 905
oxidation of, 527–528
bicyclo[5.2.0]octa-3,5-diene
reactions of, 526–529
Cope rearrangement of, 927
reduction of ketones by, 193–194
bicyclo[6.2.0]deca-1,3,5,7,9-pentaene, 753–4
allyl, facile 1,3-sigmatropic shift
BINAP, see bis-2,2’-(diphenylphosphinyl)-1,1’-
in, 916
binaphthalene
chloro
1,1’-binaphthalene-2,2’-diol
reduction of ketones by, 193–194
chirality of, 130
halo
derivatives as catalysts for enantioselective
hydroboration by, 524, 531
Diels-Alder reactions, 868
as radical sources, 979
1,1’-binaphthyl derivatives
borohydrides, alkyl
chirality of, 129–130
in reduction of ketones, 193
BINOL, see 1,1’-binaphthalene-2,2’-diol
boron enolates
biphenylene, 824
in aldol reactions, 690–691
bis-2,2’-(diphenylphosphinyl)-1,1’-binaphthalene
of amides, 693
chirality of, 130
of esters, 693
as ligand in enantioselective hydrogenation, 190
of N-acyloxazolidinones
bis-oxazoline catalysts
in aldol reactions, 694–695
for aldol reaction, 696
boron trifluoride
for enantioselective Diels-Alder reactions,
867–868 complex with 2-methylpropenal, 849
bond angles as Lewis acid catalyst, 354
in relation to hybridization, 4–5, 87 BOX catalysts, see bis-oxazolines
bond critical point, AIM definition, 63 BPE, see phosphines
bond dipole, 10 bromination, see also halogenation
bond dissociation energy, 257–258 of alkenes
computation of, 318 mechanism of, 486–489
electronegativity effect on, 14, 259–260 reagents for, 491
of halogens, 258–259 stereospecificity of, 183–185
relationship to radical stability, 312–313, 317, allylic, 1020–1021
1052–1055 of aromatic compounds, 802–803
relation to hybridization, 259–260 substituent effects on, 290–293
in relation to hydrogen abstraction reactions, of butene, kinetic isotope effect, 335
1001 by N-bromosuccinimide, 1020–1
table of, 258, 1053 by radical substitution, 1018–24
bond energy, see also bond dissociation examples, 1002–4
energy of dienes, 496–497
intrinsic, 1053 bromohydrins
in substituted carbonyl compounds, 321 formation of, 492