Summary
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1.
In presence of azodiisobutyronitrile (AN) benzenethiol forms addition products with N-alkenyl lactams in lower yields than aliphatic thiols do. N-Allyl lactams form the products of free-radical addition (in the direction opposite to that required by Markovnikov's rule).
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2.
The addition of benzenethiol to N-vinyl lactams was studied under various initiation conditions. The highest yield of adducts is attained by initiation of the reaction with hydrochloric acid. Irrespective of the nature of the initiator (even AN), ionic electrophilic addition of benzenethiol occurs, and this is the first time that this phenomenon has been met with this substance.
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3.
The structures of the addition products were proved by chemical and spectroscopic methods. It was shown that N-l- and N-2-(phenylthio)ethyl lactams can be identified with the aid of ultraviolet absorption spectra.
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Sidel'kovskaya, F.P., Kolodkin, F.L., Andrianova, G.M. et al. Lactones and lactams. Russ Chem Bull 11, 1542–1548 (1962). https://doi.org/10.1007/BF00907232
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DOI: https://doi.org/10.1007/BF00907232