Rearrangements and Reactions of Stable Sulfonium Ylids from Acetylenic Sulfonium Salts

Autor:	Atsusuke Terada, Yukichi Kishida
Rok vydání:	1970
Předmět:	Dimethyl acetylenedicarboxylate Ethyl propiolate chemistry.chemical_compound Ethanol Nucleophile chemistry Sulfonium Drug Discovery Organic chemistry General Chemistry General Medicine Phenylisocyanate
Zdroj:	Chemical and Pharmaceutical Bulletin. 18:505-510
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.18.505
Popis:	Dimethylsulfonium 2-oxo-3, 4-diphenyl-3-butenylide derivatives (Ia-c) rearranged in boiling ethanol, in a Pummerer-type fashion, to produce 1, 2-diphenyl-3-methylthiomethoxy-1, 3-butadiene (IVa-c). Nucleophilicity of the ylid (I) was examined by the reactions described below. I-a still reacted with dimethyl acetylenedicarboxylate and ethyl propiolate to afford new stable ylids of dimethylsulfonium 1, 2-dimethoxycarbonyl-4-oxo-5, 6-diphenyl-1, 5-hexadien-3-ylide (IX) and dimethylsulfonium 1-ethoxycarbonyl-4-oxo-5, 6-diphenyl-1, 5-hexadien-3-ylide (X), respectively. I also reacted with phenylisocyanate derivatives forming stable ylids, dimethylsulfonium 1-phenylcarbamoyl-2-oxo-3, 4-diphenyl-3-butenylide derivatives (XIa-e).
Databáze:	OpenAIRE
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