The synthesis and properties of annulene polyoxides

Abstract

A convenient synthesis of the higher annulene polyoxides is described. Sucrose was converted into 5-chloromethylfurfural which on reaction with triphenylphosphine gave the corresponding phosphonium salt. Treatment of this salt with lithium ethoxide accomplished a self-Wittig condensation and cyclic products isolated included [18]annulene trioxide, two isomers of [24]annulene tetroxide, two isomers of [30]annulene pentoxide, and an isomer of [36]annulene hexoxide. The properties of these compounds are discussed in relation to their aromaticity.