Fragmentation and isomerization reactions of phenyl substituted 2??oxo??1, 3, 2??dioxathianes (trimethylene sulfites)

RJ Olsen, TA Lewis, MA Mehta…

Index: Olsen, Robert J.; Lewis, Timothy A.; Mehta, Manish A.; Stack, Jeffrey G. Journal of Heterocyclic Chemistry, 1986 ,  vol. 23, p. 1099 - 1102

Full Text: HTML

Citation Number: 3

Abstract

Abstract The preparation and Grob-like fragmentation of several phenyl substituted 2-oxo-1, 3, 2-dioxathianes (trimethylene sulfites) have been examined. Preparation of the 4, 4, 6- triphenyl derivatives gives a chair S= O equatorial isomer which fragments readily in polar solvents to produce benzaldehyde and 1, 1-diphenylethylene. Isomerization to an unreactive twist boat isomer occurs as a minor reaction in solution and in the solid state on ...