The synthesis and properties of annulene polyoxides
- 1 January 1969
- journal article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 22 (9) , 1951-1962
- https://doi.org/10.1071/ch9691951
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.Keywords
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