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Paper | Regular issue | Vol 29, No. 12, 1989, pp.2345-2351
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5122
The Skraup Reaction of 3,4-Dihydroanilines

Richard A. Blatchly, Michael A. Greeley, and J. Hodge Markgraf*

*Department of Chemistry, Williams College, 47 Lab Campus Drive, Williamstown, MA 01267, U.S.A.


Six 3,4-dithaloanilines (1) were converted by the sulfo-mix variation of the Skrap reaction to mixtures of 5,6- and 6,7-dihaloquinolines, 2 and 3 respectively. Inductive effects were the dominant influence on the course of cyclization: the more highly electronwithdrawing the substituents of 1, the greater was the proportion of 3. Steric effects were absent.