FACTORS WHICH CONTROL PI-FACIAL SELECTION IN THE REDUCTION OF 5-SUBSTITUTED ADAMANTANONES

被引：66

作者：

COXON, JM

HOUK, KN

LUIBRAND, RT

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

[2] CALIF STATE UNIV HAYWARD,DEPT CHEM,HAYWARD,CA 94542

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 02期

关键词：

D O I：

10.1021/jo00107a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ab initio and semiempirical calculations of the transition states for reduction of 5-substituted adamantanones with AlH3 show bond lengthening and molecular orbitals consistent with hyperconjugative stabilization. Electronic as well as torsional effects contribute to facial selection.

引用

页码：418 / 427

页数：10

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