Journal of Organic Chemistry p. 43 - 46 (1993)
Update date:2022-07-30
Topics:
Collazo, Luis R.
Guziec, Frank S.
Two-fold extrusion reactions of 1,3,4-thiadiazolines 1 provide a convenient stereoselective route to unhindered Z-olefins.An improved preparation of the thiadiazolines involves reaction of an aldehyde with H2S-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 Z-alkene in good yields.
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