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Regiospecific Syntheses of Sulfoxides and Sulfones of the ( Z )‐Configuration
Author(s) -
Liu Lilian Kao,
Luo FenTair,
Shia SeeYing
Publication year - 1982
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198200004
Subject(s) - chemistry , phenylacetylene , acetic acid , hydrogen peroxide , alkyl , catalysis , sodium , zinc , medicinal chemistry , organic chemistry , chloride
A convenient synthesis for varions ( Z )‐1‐alkanesulfinyl‐2‐phenylethenes has been developed. This involves addition of different sodium thiolates to phenylacetylene in ethanol, and oxidation of the resulting ( Z )‐1‐alkanesulfenyl‐2‐phenylethenes [( Z )‐styryl alkyl thioethers] with sodium metaperiodate supported on acidic alumina. The corresponding sulfones can be obtained by oxidation of these ( Z )‐styryl alkyl thioethers with hydrogen peroxide in glycial acetic acid, or, alternatively by reduction of the β‐iodostyrylsulfones with zinc in acetic acid. These β‐iodostyrylsulfones were obtained by addition of the corresponding sulfonyl iodides to phenylacetylene under the catalytic action of cupric chloride and triethylaminium chloride.