
%0 Journal Article
%A Elix, JA 
%T The synthesis and properties of annulene polyoxides
%J Australian Journal of Chemistry
%D 1969/09/01
%V 22
%N 9
%P 1951-1962
%K 
%R https://doi.org/10.1071/CH9691951
%U https://www.publish.csiro.au/paper/CH9691951 
%X 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. 
