ON THE REGIOSELECTIVITY IN TRANSFORMATION OF BENZO[A]PYRENE 4,5-OXIDE AND 3-METHYLCHOLANTHRENE 11,12-OXIDE TO THE CORRESPONDING BETA-AMINO-ALCOHOL DERIVATIVES

被引：4

作者：

BLUM, J ^{[1
]}

SETTYFICHMAN, M ^{[1
]}

EFRON, L ^{[1
]}

SHAIK, S ^{[1
]}

HARVEY, RG ^{[1
]}

机构：

[1] UNIV CHICAGO,BEN MAY INST,CHICAGO,IL 60637

来源：

TETRAHEDRON | 1994年 / 50卷 / 28期

关键词：

D O I：

10.1016/S0040-4020(01)85570-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Amino-alcohol derivatives of benzo[a]pyrene and 3-methylcholanthrene, 8, 9 and 15 which are assumed to take part in the transformation of the K-region oxides 1 and 10 to the corresponding arene imines, have been prepared. The sequence of reactions consists of nucleophilic oxirane ring opening of the epoxides by azide ion, acetylation of the separated isomeric trans-azido alcohols so formed, and palladium catalyzed hydrogenation of the resulting beta-acetyloxy azides under ambient conditions. The ratios between the isomeric azido-hydrins obtained from 1 and 10, as well as the product distribution in azide-induced oxirane ring cleavage in other carbocyclic and heterocyclic arene oxides have been shown to correlate with Huckel-type calculations of Wheland's pi-localization energies.

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页码：8505 / 8514

页数：10

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