THE DIFFERENCE IN STRENGTH OF BF3-COMPLEXES OF AROMATIC AND ALIPHATIC-ALDEHYDES

被引：35

作者：

GUNG, BW

机构：

[1] Department of Chemistry, Miami University, Oxford

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 25期

关键词：

D O I：

10.1016/0040-4039(91)80634-I

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

ab initio MO computations have shown that the difference in energy between syn and anti complexation is much larger for benzaldehyde/BF3 than for acetaldehyde/BF3. The B-O bond strength is much greater for the anti PhCHO.BF3 than for its syn isomer and for all the CH3CHO.BF3 complexes.

引用

页码：2867 / 2870

页数：4

共 12 条

[1] SNCL4(4-TERT-BUC6H4CHO)2 - X-RAY CRYSTAL-STRUCTURE, SOLUTION NMR, AND IMPLICATIONS FOR REACTIONS AT COMPLEXED CARBONYLS
DENMARK, SE
HENKE, BR
WEBER, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) : 2512 - 2514
[2] FRISCH MJ, GAUSSIAN 88
[3] AN ABINITIO MOLECULAR-ORBITAL EVALUATION OF LEWIS ACID CATALYSIS ON DIELS-ALDER REACTIONS OF ACROLEIN
GUNER, OF
OTTENBRITE, RM
SHILLADY, DD
ALSTON, PV
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) : 391 - 394
[4] AN ANOMALOUS CASE OF DIASTEREOFACIAL SELECTIVITY IN THE ADDITION OF CHIRAL ALLYLSTANNANES TO BENZALDEHYDE - IS THE INSIDE ALKOXY EFFECT INVOLVED
GUNG, BW
PEAT, AJ
SNOOK, BM
SMITH, DT
[J]. TETRAHEDRON LETTERS, 1991, 32 (04) : 453 - 456
[5] STRONG CONFORMATIONAL CONSEQUENCES OF HYPERCONJUGATION
HOFFMANN, R
HEHRE, WJ
SALEM, L
SCHLEYER, PV
POPLE, JA
RADOM, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6221 - &
[6] CHELATION CONTROLLED DIASTEREOFACIAL SELECTIVITY IN CROTYLTRI-N-BUTYLSTANNANE ADDITIONS TO ALPHA-ALKOXYALDEHYDES
KECK, GE
BODEN, EP
[J]. TETRAHEDRON LETTERS, 1984, 25 (18) : 1879 - 1882
[7] ON THE ORIGINS OF STEREOSELECTIVITY IN CHELATION CONTROLLED NUCLEOPHILIC ADDITIONS TO BETA-ALKOXY ALDEHYDES - SOLUTION STRUCTURES OF LEWIS ACID COMPLEXES VIA NMR-SPECTROSCOPY
KECK, GE
CASTELLINO, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (13) : 3847 - 3849
[8] KECK GE, 1984, TETRAHEDRON LETT, V25, P265, DOI 10.1016/S0040-4039(00)99857-5
[9] STRUCTURE AND ELECTRONIC NATURE OF THE BENZALDEHYDE-BORON TRIFLUORIDE ADDUCT
REETZ, MT
HULLMANN, M
MASSA, W
BERGER, S
RADEMACHER, P
HEYMANNS, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) : 2405 - 2408
[10] SHAMBAYATI S, 1990, ANGEW CHEM INT EDIT, V29, P265

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