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

A Padwa, B Harrison, SS Murphree…

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

Full Text: HTML

Citation Number: 29

Abstract

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

Related Articles:

Dimerization of (e)-2-benzenesulfonyl-1, 3-alkadienes the benzenesulfonyl group exerts acyclic stereocontrol

[Hoffmann, H. Martin R.; Weichert, Andreas; Slawin, Alexandra M. Z.; Williams, D. J. Tetrahedron, 1990 , vol. 46, # 16 p. 5591 - 5602]

Dimerization of (e)-2-benzenesulfonyl-1, 3-alkadienes the benzenesulfonyl group exerts acyclic stereocontrol

[Hoffmann, H. Martin R.; Weichert, Andreas; Slawin, Alexandra M. Z.; Williams, D. J. Tetrahedron, 1990 , vol. 46, # 16 p. 5591 - 5602]

2-(Phenylsulfonyl)-1, 3-dienes as versatile synthons in organic transformations. Multicoupling reagents and Diels-Alder dienes with a dual electron demand

[Baeckvall,J.E.; Juntunen,S.K. Journal of the American Chemical Society, 1987 , vol. 109, p. 6396]

More Articles...