SOLVOLYSIS OF SPIROOCTA-1,4,7-TRIEN-6-ONES EVIDENCE OF A VINYL CATION INTERMEDIATE

Article abstract of DOI:10.1246/cl.1982.387

Ethanolysis of 1-aryl-5,7-di-t-butyl-2-phenylspiro<2.5>octa-1,4,7-trien-6-one 2 proceeds via a vinyl cation generated by opening of the cyclopropene ring, judging from regiospecific ring opening and kinetics (ρ⁺= -3.0, m = 0.53, and rate dependence on pH of the solvent).