[2,3]-Sigmatropic rearrangement of .beta.-phenylsulfonyl propargylic sulfenates as a method for preparing 1,4-bis(phenylsulfonyl)-1,3-butadienes

Autor:	Harold D. Banks, Xiaoheng Wang, Augusto Rodriguez, Andrea Hollis, Zhijie Ni, Xiujing Lu, Albert Padwa
Rok vydání:	1993
Předmět:	chemistry.chemical_compound Chemistry Thiophenol 2 3-sigmatropic rearrangement Organic Chemistry Sulfoxide Conjugated system Sigmatropic reaction Aliphatic compound Medicinal chemistry Enone Sulfone
Zdroj:	The Journal of Organic Chemistry. 58:5377-5385
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00072a019
Popis:	Several β-sulfoxy-substituted acetylenic carbinols were prepared by the addition of thiyl radicals and oxygen to conjugated enynes. The products obtained are derived from thiyl radical attack at the olefinic bond to generate a propargylic radical. Capture of this radical by oxygen followed by hydrogen transfer from thiophenol gives a hydroperoxide intermediate, which undergoes oxygen transfer by both intra- and intermolecular pathways. The resultant β-phenylsulfinyl propargylic alcohols proved to be versatile intermediates for the preparation of several different classes of compounds. The [2,3]-sigmatropic sulfinate to sulfoxide rearrangement was found to give 1,4-bis(phenylsulfonyl)1,3-butadienes, α,β-unsaturated phenylsulfoxy ketones, and β-phenylsulfonyl α-allenic sulfoxides
Databáze:	OpenAIRE
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