Generation and cycloaddition reactions of phenylsulfonyl-substituted 1, 3-butadienes

A Padwa, B Harrison, SS Murphree…

文献索引：Padwa, Albert; Harrison, Brian; Murphree, S. Shaun; Yeske, Philip E. Journal of Organic Chemistry, 1989 , vol. 54, # 17 p. 4232 - 4235

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被引用次数: 29

摘要

1 H* onto the central carbon atom of the activated allene to give disulfone 3 as a transient intermediate. This material undergoes a subsequent 1, 3-(phenylsulfonyl) shift to produce the rearranged alkene 4.14 Treatment of 4 with DBU in benzene at 25 OC afforded diene 5, which was found to undergo Diels-Alder dimerization on standing. 2 Reaction of 4 with DBU in the presence of enamine 6 proceeded