Steric and conformational effects in nicotine chemistry

JI Seeman, HV Secor, CG Chavdarian…

文献索引：Seeman, Jeffrey I.; Secor, Henry V.; Chavdarian, Charles G.; Sanders, Edward B.; Bassfield, Ronald L.; Whidby, Jerry F. Journal of Organic Chemistry, 1981 , vol. 46, # 15 p. 3040 - 3048

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被引用次数: 27

摘要

The stereoselectivity of iodomethylation of nicotine and seven nicotine analogues having pyridine alkyl groups waa determined by using I3C NMR. Alkylation at the pyridine (N) and at the pyrrolidine (N') nitrogens was observed. Two modes of N'-iodomethylation occur, cia and tram to the pyridine ring. N'-Iodomethylation occum regioselectively cis to the pyridine ring for all compounds examined. The N/N'and N'&/N'*,, ratios for the nicotinoids were ...