Constituents of cigarette smoke. Part X. Evidence for 1,5-hydrogen transfer in the formation of non-conjugated isoprenoid polyolefins during pyrolysis

Abstract

A major group of compounds present in cigarette smoke condensate are the polyolefins (I) which are not present in fresh or cured tobacco leaf. Studies on deuterium-labelled model olefins have provided evidence for specific 1,2- and 1,5-migrations of hydrogen at temperatures in the range 300–400° and suggest the role of a similar mechanism in the formation of the polyolefins (I).