The chemistry of terpenes. Part 27. The halogenation of (+)-thujone and of (–)-carvotanacetone, and the stereochemistry and mechanism of formation of ‘tribromothujone’

Abstract

The gross structure and precise stereochemistry of ‘tribromothujone’ have been identified; its adjacent bromine atoms are cis-orientated. The mechanism of its formation is discussed. A number of halogenated compounds derived from (+)-thujone have been obtained and their absolute configurations determined. (–)-Carvotanacetone dibromide and two tribromides have been stereochemically identified.