Sigmatropic Rearrangement of Ammonium Ylides—Key Step in the Synthesis of Methyl 2-Formylphenyl Acetate

Anna Kowalkowska , Andrzej Jończyk

Abstract

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.
Author Anna Kowalkowska (FC / IBC / DDTB)
Anna Kowalkowska,,
- Department Of Drug Technology And Biotechnology
, Andrzej Jończyk (FC / IBC / DDTB)
Andrzej Jończyk,,
- Department Of Drug Technology And Biotechnology
Journal seriesSynthetic Communications, ISSN 0039-7911, (A 20 pkt)
Issue year2011
Vol41
Pages3308-3317
Keywords in EnglishAmmonium salts; ammonium ylides; methyl 2-formylphenyl acetate; sigmatropicrearrangement
ASJC Classification1605 Organic Chemistry
DOIDOI:10.1080/00397911.2010.517891
Internal identifier4365
Languageen angielski
Score (nominal)20
Publication indicators Scopus Citations = 6; WoS Citations = 6; Scopus SNIP (Source Normalised Impact per Paper): 2014 = 0.462; WoS Impact Factor: 2011 = 1.062 (2) - 2011=1.091 (5)
Citation count*4 (2015-03-19)
Cite
Share Share

Get link to the record


* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
Back
Confirmation
Are you sure?