SELECTIVE REDUCTIONS .13. REACTION OF DELTA2-CYCLOPENTENONES WITH REPRESENTATIVE COMPLEX HYDRIDES . ALUMINUM HYDRIDE AS A SELECTIVE REAGENT FOR REDUCTION OF CARBONYL GROUP IN DELTA2-CYCLOPENTENONES

被引：134

作者：

BROWN, HC

HESS, HM

机构：

[1] Richard B. Wetherill Laboratory of Purdue University, Lafayette

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 07期

关键词：

D O I：

10.1021/jo01259a039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of 2-cyclopenten-1-one and 5,6-dihydro-erado-dicyclopentadien-1-one with metal hydrides takes place with considerable concomitant saturation of the double bond. However, the inverse addition of 0.667 mole equiv of aluminum hydride to 2-cyclopenten-1-one, 3-substituted 2-cyclopenten-1-ones, 5,6-dihydro-endo-dicyclopentadien-1-one, and 3-substituted 5,6-dihydro-endo-dicyclopentadien-1-ones, produces the unsaturated carbinols in satisfactory purity and yield and thus provides an effective route for the selective reduction of the carbonyl group in ∆2-cyclopentenones. © 1969, American Chemical Society. All rights reserved.

引用

页码：2206 / &

共 22 条

[1] EXPERIMENTS BEARING ON THE SYNTHESIS OF CORTISONE .1. SOME CYCLOPENTENONE DERIVATIVES [J].