Regular Issue

Vol. 22, No. 1, 1984

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Review | Regular issue | Vol 22, No. 1, 1984, pp.165-193
Published online:
DOI: 10.3987/R-1984-01-0165
■ Recent Studies in Nicotine Chemistry. Conformational Analysis, Chemical Reactivity Studies, and Theoretical Modeling

Jeffrey I. Seeman*

*Research Center, Philip Morris USA, P.O. Box 26853, Rcihmond, Vierginia 23261, U.S.A.

Abstract

The synthesis in our laboratories of a wide variety of nicotine analogues has served as the basis for a range of chemical investigations. We have examined the effect of substituents on nicotine’s structure, conformation, and chemical reactivity. The methylation of nicotine and a wide variety of nicotine analogues has been studied. Three modes of alkylation are observed: pyridine and pyrrolidine, the latter occurring either cis or trans to the pyridine ring. The results of these alkylations are evaluated in terms of the Curtin-Hammett principle and the Winstein-Holness equation. Attention is focused on the effect of conformation on chemical reactivity. Ground state and transition state reactivity modes of the Menschutkin reaction are presented.

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Review | Regular issue | Vol 22, No. 1, 1984, pp.195-221
Published online:
DOI: 10.3987/R-1984-01-0195
■ The Leimgruber-Batcho Indole Synthesis

Robin D. Clark and David B. Repke

*Institute of Organic Chemistry, Syntex Research, Palo Alto, California 94304, U.S.A.

Abstract

The Leimgruber-Batcho indole synthesis, which involves the reduction of β-dimethylamino-2-nitrostyrenes, is reviewed along with applications and modifications thereof.

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