REACTIONS OF ALKYLBENZYLDIMETHYLAMMONIUM HALIDES WITH AMIDE IN LIQUID-AMMONIA

被引:11
作者
BUMGARDNER, CL
HSU, HB
AFGHAHI, F
ROBERTS, WL
PURRINGTON, ST
机构
[1] Department of Chemistry, North Carolina State University, Raleigh
关键词
D O I
10.1021/jo01328a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Competitive elimination and rearrangement reactions of alkylbenzyldimethylammonium ions with amide ion in liquid ammonia have been investigated. Elimination is largely dependent on the geometry of the alkyl group. Cyclohexyl-and tert-butylbenzyldimethylammonium halides undergo more Stevens than Sommelet-Hauser rearrangement with amide ion in liquid ammonia. The results are interpreted in light of the reactivity of the intermediate ylide. The structure of the rearrangement product from isopropylbenzyldimethylammonium iodide has been reassigned. © 1979, American Chemical Society. All rights reserved.
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页码:2348 / 2353
页数:6
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