Unexpected reductive double carbon-carbon bonds cleavage of bicyclic nitrocyclopropanes

被引：3
|
作者：
Kamimura, Akio [1 ]
Ikeda, Kosuke [1 ]
Moriyama, Takaaki [1 ]
Uno, Hidemitsu [2 ]
机构：
[1] Yamaguchi Univ, Grad Sch Med, Dept Appl Mol Biosci, Ube, Yamaguchi 7558611, Japan
[2] Ehime Univ, Grad Sch Sci & Engn, Dept Chem, Matsuyama, Ehime 7908577, Japan
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 14期
关键词：
Nitrocyclopropanes; Carbon-carbon bond cleavage; Vinyl nitriles; Oximes; PRIMARY NITRO-COMPOUNDS; ALPHA-AMINO-ACIDS; STEREOSELECTIVE-SYNTHESIS; SYNTHETIC METHODS; NITRILES; CYCLOPROPANATION; NITROCOMPOUNDS; CONVERSION; EXPEDIENT; ALKENES;
D O I：
10.1016/j.tetlet.2013.01.094
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reductive treatment of bicyclic nitrocyclopropanes with zinc powder under acidic conditions resulted in the double cleavage of carbon-carbon bonds in the cyclopropane to give vinyl nitrile in good yields. The reductive cleavage of carbon-carbon bond depended on the reaction conditions and sufficient acidic treatment gave alkenyl nitriles in good yields, while weak acidic treatment afforded oxime derivative instead. (C) 2013 Elsevier Ltd. All rights reserved.
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页码：1842 / 1844
页数：3
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