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ChemInform Abstract: “syn-Effect” in the Desulfonylation Reaction of α,α- Dialkylated (E)-Allylic Sulfones.

✍ Scribed by A. SHIBAYAMA; T. NAKAMURA; T. ASADA; T. SHINTANI; Y. UKAJI; H. KINOSHITA; K. INOMATA

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

syn-Effect" in the Desulfonylation Reaction of α,α-Dialkylated (E)-Allylic Sulfones.

-Desulfonation of the title compounds, e.g. (I) and (IV), with a base furnishes preferentially the sterically unfavorable (Z)alkadienes. The relative degree of the "syn-effect", defined as effect stabilizing the syn-conformation and leading to (Z)-products, in the transition state against the steric hindrance is revealed for various substituents at the δ-position of the (E)-allylic sulfones to be as follows: R

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