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Communication | Regular issue | Vol 16, No. 3, 1981, pp.367-369
Published online, 1st January, 1970
DOI: 10.3987/R-1981-03-0367
Bimolecular Products from the Reduction of Quinolines with Zinc and Hydrochloric Acid

I. Wesley Elliott,* Charles R. Montgomery, and Peter Yates

*Department of Chemistry, Fisk University, Nashville, Tennessee 37203, U.S.A.

Abstract

Comparison of the 13C nuclear magnetic resonance spectra of the bimolecular products 4a-4c obtained on reduction of 2-methylquinoline, 2,4-dimethylquinoline, and 6-bromo-2-methylquinoline, respectively, with zinc and hydrochloric acid with the spectra of the corresponding products from 8-methoxy-2-methylquinoline and 6-chloro-2-methylquinoline shows that the latter have the analogous bridged ring structures 4d and 4e, respectively, and not fused cyclobutanoid structures of type 1.