(Phenylsulfonyl) allenes as Substrates for Cycloaddition Reactions: Intramolecular Cyclizations onto Unactivated Alkenes

…, M Meske, SS Murphree, SH Watterson…

Index: Padwa, Albert; Meske, Michael; Murphree, S. Shaun; Watterson, Scott H.; Ni, Zhijie Journal of the American Chemical Society, 1995 , vol. 117, # 27 p. 7071 - 7080

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Citation Number: 68

Abstract

Abstract: The reaction of a series of allyl-substituted bis (phenylsulfony1) methanes or dimethyl malonates with 2, 3-bis (phenylsulfony1)-1, 3-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene, and this is followed by PhSO2- elimination to give the phenylsulfonyl-substituted allene. Themal [2+ 21-cycloaddition ...

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