SIGMATROPIC REARRANGEMENT OF AMMONIUM YLIDES-KEY STEP IN THE SYNTHESIS OF METHYL 2-FORMYLPHENYL ACETATE

被引：7

作者：

Kowalkowska, Anna ^{[1
]}

Jonczyk, Andrzej ^{[1
]}

机构：

[1] Warsaw Univ Technol, Fac Chem, PL-00662 Warsaw, Poland

来源：

SYNTHETIC COMMUNICATIONS | 2011年 / 41卷 / 22期

关键词：

Ammonium salts; ammonium ylides; methyl 2-formylphenyl acetate; sigmatropic rearrangement; PHOTOCHEMISTRY; ANALOGS;

D O I：

10.1080/00397911.2010.517891

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Cyanomethyl-N,N-dimethyl-N-(a-methoxycarbonyl) benzylammonium salts 5 were synthesized and treated with different base/solvent systems, giving the products of sigmatropic rearrangements [2,3] 7 and [1,2] 8. In reactions carried out in liquid ammonia, [2,3] rearrangement definitively prevailed. Pure 7(or mixture of 7 and 8) were deprotected to afford methyl 2-formylphenyl acetate (9) in good yield.

引用

页码：3308 / 3317

页数：10

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