73920-79-3Relevant academic research and scientific papers
Contributions to the Chlorination-Dehydrochlorination of Perhydro-1,4-thiazepin-5-ones
Wamhoff, Heinrich,Theis, Christoph H.
, p. 995 - 1009 (2007/10/02)
The synthesis of unsaturated derivatives of perhydro-1,4-thiazepin-5-ones 3 is investigated.Depending on the substitution the thiazepin-5-ones 3 thereby react with sulfuryl chloride to yield 7-and 2-chloro derivatives 6 and 7; the latter eliminate hydrogen chloride only in the presence of a base (PVP, 8) to give the Δ2-thiazepines 9a,b,d,e,g, whereas the 7-chloro derivatives in situ afford the Δ6-thiazepines 10a - f, the 1,4-thiazepinium chloride 11c being isolated as intermediate. tert-Butyl hypochlorite forms according to the substituent size and solvent polarity 2- and 7-halogenation products, as well as 1,4-thiazepin-5-one-S-oxides 22.Further halogenation of the Δ6-1,4-thiazepines 10a - c results in the formation of unsaturated halogen derivatives 24, 25, and 26.
