Synthesis and silica gel-catalysed decomposition of 3-(1-arylcycloalkyl)substituted 1,2,4-trioxolanes and 1,2,4-dioxazolidines

Abstract

Decomposition of 3-(1-phenylcyclopentyl)- and 3-(1 -phenylcyclohexyl)-4-benzyl-5-phenyl-1, 2, 4-dioxazolidines, derived from [3 + 2] cycloadditions of benzaldehyde O-oxide and imines, by silica gel gave mixtures of the corresponding phenylcycloalkene, benzaldehyde, and N-benzylformamide. In the case of 3-(1-arylcyclopentyl)- and 3-(1-phenylcyclohexyl)-substituted 1, 2, 4-trioxolanes also, a similar mode of decomposition was observed. A mechanism involving heterolytic fission of the C–C bond between the peroxide ring and the cycloalkyl substituent, is proposed.