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An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
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Announcement
Yoshito Kishi (1937-2023)

Professor. Yoshito Kishi,
a member of the Honorary Editorial Associates of HETEROCYCLES,
has passed away on January 9, 2023 at the age of 85.
I deeply express my regret over his death.
Kunio Ogasawara
Editor
January 13, 2023
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December 24, 2019
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Regular Issue
Vol. 22, No. 1, 1984
Published online:
■ 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.
Published online:
■ 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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