On the structure of the sex attractant of the American cockroach

Abstract

The structure 2,2-dimethyl-3-isopropylidenecyclopropyl propionate has been proposed for the pheromone of the cockroach Periplaneta americana(L). Rational synthesis of this compound and comparison with published data definitely disprove this attribution. The route used involved addition of 2-diazopropane to 3-methylbuta-1,2-dienyl propionate, photolysis of the crystalline adduct, and separation from the isomeric tetramethylcyclopropylidenemethyl propionate which was formed simultaneously.