Convenient preparation of 1, 1-disubstituted olefins from primary tosylates and iodides

S Wolff, ME Huecas, WC Agosta

Index: Wolff, Steven; Huecas, Maria Esperanza; Agosta, William C. Journal of Organic Chemistry, 1982 , vol. 47, # 22 p. 4358 - 4359

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Citation Number: 20

Abstract

The failure of l-octyl tosylate (6) to furnish a serviceable yield of l-octene in procedure B is in agreement with the original report noted above. Treatment of cyclohexanemethyl tosylate (3) directly with DBU (as procedure B, but not sodium iodide) failed to give methylenecyclohexane. With suitable activation, however, the direct elimination of p- toluenesulfonic acid is feasible under mild conditions, as is shown by entry 7. Procedure C ...