Conversion of allyl alcohols to 1, 3-dienes by sequential sulfenate sulfoxide [2, 3]-sigmatropic rearrangement and syn-elimination

HJ Reich, S Wollowitz

Index: Reich,H.J.; Wollowitz,S. Journal of the American Chemical Society, 1982 , vol. 104, p. 7051

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Citation Number: 71

Abstract

Abstract: A method for the 1, 4 dehydration of allyl alcohols to give 1, 3-dienes has been developed. The technique involves treatment of the allyl alcohol with 2, 4- dinitrobenzenesulfenyl chloride and triethylamine. The sulfenate ester so formed undergoes [2, 3] sigmatropic rearrangement to the isomeric allylic sulfoxide, followed by thermal syn elimination to give a diene. A number of different systems were studied to establish the ...