The Journal of Organic Chemistry

Substitution at tricoordinate sulfur (IV). Rearrangement of sulfinanilides to anilino sulfoxides

KK Andersen, O Malver

Index: Andersen, Kenneth K.; Malver, Olaf Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 4803 - 4807

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Citation Number: 3

Abstract

5, Ph; 6, 3-C1C6H4; 7, 3-FC6H4), N-(3-methoxyphenyl)-p-toluenesulfinamide (8), and two N- methyl-N-arylmethanesulfinamides (9, 3-Me2NC6H4; 10, 3-MeOC6H4) were prepared from the corresponding sulfinyl chloride and the substituted aniline. Sulfinanilides 2 and 7 were treated with alkyllithiums in vain attempts to induce rearrangement to the diary1 sulfoxides via endocyclic nucleophilic attack by carbon 2 of the aniline ring on sulfur. Instead, the ...