SELECTIVE REDUCTIONS .14. FAST REACTION OF ARYL BROMIDES AND IODIDES WITH LITHIUM ALUMINUM HYDRIDE IN TETRAHYDROFURAN . A SIMPLE, CONVENIENT PROCEDURE FOR HYDROGENOLYSIS OF ARYL BROMIDES AND IODIDES

被引:99
作者
BROWN, HC
KRISHNAM.S
机构
[1] Richard B. Wetherill Laboratory, Purdue University, Lafayette
关键词
D O I
10.1021/jo01264a037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unactivated aromatic bromides are reduced quite rapidly and quantitatively to the corresponding hydrocarbons by lithium aluminum hydride in refluxing tetrahydrofuran. Iodides are reduced at a reasonable rate even at room temperature. The ease of reduction of the different halogens, as indicated by rate studies, follows the order I > Br > Cl > F. Iodo and bromo substituents can be selectively removed in the presence of chloro substituents. This provides a convenient synthetic procedure for debromination and deiodination of aryl halides where this is required in synthetic operations. © 1969, American Chemical Society. All rights reserved.
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页码:3918 / &
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