Tetrahedron Letters p. 2483 - 2486 (1993)
Update date:2022-08-02
Topics:
Alvernhe, Gerard M.
Laurent, Andre J.
Drean, Isabelle M. Le
Selmi, Abdelaziz
β-Trifluoromethyl β-chloroacrolein 2 reacts with 2-mercaptoethylamine 3 to produce thiazolidine 5 instead of the expected thiazepine 8.The reason of this behaviour is the formation of the tetrahedral intermediate 6 because of stabilisation by the trifluoromethyl group; an intramolecular substitution takes place faster than a 1,4 addition-elimination process. Key Words: Trifluoromethyl; Michael reaction; regiochemistry; thiazolidine; thiazepine
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