Summary
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1.
The free-radical-induced addition of hydrogen sulfide to N-vinyl lactams was studied, and it was shown that sulfides and thiols can be prepared from N-vinylcaprolactam and 1-vinyl 2-pyrrolidinone in this way in overall yields of 75–85 %.
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2.
It was shown that the second stage of the process is the faster, so that the sulfide is preferentially formed. Synthesis of the thiol from N-vinylcaprolactam in 40–45 to yield was effected by the use of an 11–13-fold molar excess of hydrogen sulfide.
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Shostakovskii, M.F., Shapiro, E.S. & Sidel'kovskaia, F.P. Investigation of lactones and lactams Communication 10. Addition of hydrogen sulfide to N-vinyl lactams. Russ Chem Bull 7, 60–65 (1958). https://doi.org/10.1007/BF01170863
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DOI: https://doi.org/10.1007/BF01170863