Studies on the syntheses of azonia-azulenes and related compounds

Collington, Eric W

Abstract

Some substituted azonia-azulenes have been prepared for the first time. The synthetic route involves the
double elimination of hydrogen bromide from the appropriate a,a-dibromoketone using lithium chloride in dimethylformamide. Attempts have been made to synthesise the unsubstituted azoniaazulenes from the intermediate azepinones but these were not successful.
A brief review is given of the uses of lithium halides in dimethylformamide as reagents for elimination.
The double dehydrobromination reaction has been extended to give a new synthesis of benzo[2,3]tropones and related systems. Investigations into the mechanism of elimination have been carried out and a possible reaction pathway proposed.

Studies on the syntheses of azonia-azulenes and related compounds

Collington, Eric W

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Abstract

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