DIRECTED LITHIATIONS - THE EFFECT OF VARYING DIRECTING GROUP ORIENTATION ON COMPETITIVE EFFICIENCIES FOR A SERIES OF TERTIARY AMIDE, SECONDARY AMIDE, AND ALKOXIDE DIRECTED ORTHO LITHIATIONS

被引：88

作者：

BEAK, P

KERRICK, ST

GALLAGHER, DJ

机构：

[1] Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 23期

关键词：

D O I：

10.1021/ja00076a022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Significant differences for competitive efficiencies in directed ortho lithiations for single functional groups in three series, the secondary benzamides 1-4, the tertiary benzamides 5-11, and the benzylic alcohols 12-17, are reported. For both amide series the efficiencies increase as the oxygen and ortho hydrogen in the substrate are more coplanar with the aromatic ring; however, for the alcohol series the opposite order is observed. Rationalizations are offered for these observations.

引用

页码：10628 / 10636

页数：9

共 38 条

[11] BERG U, 1989, ADV PHYSICAL ORGANIC, V25, P75
[12] SOURCE OF [M-1] PEAK IN SPECTRUM OF N,N-DIMETHYLBENZAMIDE
BIELLMANN, JF
HIRTH, CG
[J]. ORGANIC MASS SPECTROMETRY, 1969, 2 (07): : 723 - +
[13] ALPHA-OXYGEN-SUBSTITUTED ORGANOLITHIUM COMPOUNDS AND THEIR CARBENOID NATURE - CALCULATIONS OF THE CONFIGURATIONAL STABILITY AND OF LICH2OH MODEL STRUCTURES, CRYSTAL-STRUCTURE OF DIPHENYL(TRIMETHYLSILYLOXY)METHYLLITHIUM.3 THF, AND THE STEREOCHEMISTRY OF THE (REVERSE) BROOK REARRANGEMENT
BOCHE, G
OPEL, A
MARSCH, M
HARMS, K
HALLER, F
LOHRENZ, JCW
THUMMLER, C
KOCH, W
[J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (10): : 2265 - 2273
[14] CONTRIBUTIONS OF CRYSTAL-STRUCTURES, MOLECULAR ELECTROSTATIC POTENTIAL MAPS, AND LIPOPHILICITY DATA TO STRUCTURE-ACTIVITY-RELATIONSHIPS OF SOME CONFORMATIONALLY RESTRICTED NORTROPANE BENZAMIDE NEUROLEPTICS
COLLIN, S
PATINY, A
VERCAUTEREN, DP
NORBERG, B
EVRARD, G
DURANT, F
[J]. JOURNAL OF CRYSTALLOGRAPHIC AND SPECTROSCOPIC RESEARCH, 1991, 21 (04): : 431 - 443
[15] IS N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE A GOOD LIGAND FOR LITHIUM
COLLUM, DB
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (10) : 448 - 454
[16] LIQUID-CHROMATOGRAPHY ON TRIACETYLCELLULOSE .14. CHROMATOGRAPHIC-SEPARATION OF ENANTIOMERS AND BARRIERS TO ENANTIOMERIZATION OF AXIALLY CHIRAL AROMATIC CARBOXAMIDES
CUYEGKENG, MA
MANNSCHRECK, A
[J]. CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (05): : 803 - 809
[17] MASS-SPECTROMETRY IN STRUCTURAL AND STEREOCHEMICAL PROBLEMS .237. ELECTRON-IMPACT-INDUCED HYDROGEN LOSSES AND MIGRATIONS IN SOME AROMATIC AMIDES
DUFFIELD, AM
DEMARTIN.G
DJERASSI, C
[J]. ORGANIC MASS SPECTROMETRY, 1974, 9 (01): : 137 - 147
[18] ORTHO LITHIATION OF MONOSUBSTITUTED BENZENES - A QUANTITATIVE-DETERMINATION OF PKA VALUES IN TETRAHYDROFURAN
FRASER, RR
BRESSE, M
MANSOUR, TS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) : 7790 - 7791
[19] CYCLOPROPYLCARBINYL CATION CHEMISTRY AND ANTI-HOMOAROMATICITY IN CYCLOPROP[2,3]INDEN-1-YL CATION SYSTEM
FRIEDRICH, EC
TAGGART, DB
SALEH, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (08) : 1437 - 1443
[20] FRITZ H, 1978, B SOC CHIM BELG, V87, P525

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