Dynamic NMR Study of the Rotation around “Biphenyl-Type” Bonds in Polycyclic Sulfoxides

S Braverman, Y Zafrani, HE Gottlieb

Index: Braverman, Samuel; Zafrani, Yossi; Gottlieb, Hugo E. Journal of Organic Chemistry, 2002 , vol. 67, # 10 p. 3277 - 3283

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Citation Number: 12

Abstract

In a recent paper, we reported on the base-catalyzed rearrangement of bis-propargylic sulfoxides that eventually leads to polycyclic products featuring an unsaturated, cyclic substituent such as cyclohexenyl or phenyl. Due to steric constraints, the latter is positioned roughly perpendicularly to the tricyclic core, and in most cases, two rotamers can be observed in the ground state. In the present work, we report on the synthesis and the ...