The Journal of Organic Chemistry

Stereoselective synthesis of unhindered olefins by 2-fold extrusion reactions

LR Collazo, FS Guziec Jr

Index: Collazo, Luis R.; Guziec, Frank S. Journal of Organic Chemistry, 1993 , vol. 58, # 1 p. 43 - 46

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Citation Number: 9

Abstract

Two-fold extrusion reactions of 1, 3, 4-thiadiazolines 1 provide a convenient stereoselective route to unhindered 2-olefins. An improved preparation of the thiadiazolines involves reaction of an aldehyde with HS-hydrazine, followed by in situ oxidation of the intermediate predominantly trans thiadiazolidine 2. Stereospecific extrusion of nitrogen yields the cis- thiirane which upon treatment with triphenylphosphine affords the corresponding 2-alkene ...