1‐Thiacyclooct‐4‐yne (=5,6‐Didehydro‐3,4,7,8‐tetrahydro‐2H‐thiocin), and Its Sulfoxide and Its Sulfone
Helvetica Chimica Acta2013Vol. 96(2), pp. 228–238
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Abstract
Abstract 1‐Thiacyclooct‐4‐yne (=5,6‐didehydro‐3,4,7,8‐tetrahydro‐2 H ‐thiocin; 9 ) can be prepared from thiocan‐5‐one ( 6 ) in three steps by applying the so‐called selenadiazole method. The heterocyclic alkyne can be oxidized to the corresponding sulfoxide 16 and sulfone 17 . Due to their geometrical strain, all three cyclic alkynes show high reactivities in DielsAlder and 1,3‐dipolar cycloadditions. Moreover, tetrathiafulvalenes can be prepared from 9 and 16 by the reaction with CS 2 .
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