Journal of the American Chemical Society

The Isomerization by Base of Alkyl Allyl Sulfides to Alkyl Propenyl Sulfides. The Mechanism of the Reaction1

DS Tarbell, WE Lovett

Index: Tarbell; Lovett Journal of the American Chemical Society, 1956 , vol. 78, p. 2259,2262

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Citation Number: 56

Abstract

Allyl n-hexyl sulfide is isomerized to n-hexyl propenyl sulfide by refluxing with 3.7 M alcoholic sodium ethoxide; allyl t-butyl sulfide behaves similarly. Diallyl sulfide is isomerized to dipropenyl sulfide, and is also converted in part to an unsaturated mercaptan, 3-mercapto- 1, 5-hexadiene, by a rearrangement of an allyl group. N-Sodiochloro-p- bromobenzenesulfonamide has been found to be superior to chloramine-T for ...