Studies of heteroaromaticity. Part LXV. Reactions of valence tautomers of three medium-sized ring unsaturated compounds with iodine azide

Abstract

Reactions of valence tautomers of cyclononatetraene. trans-7,8-dibromocyclo-octa-1,3,5-triene, and 7-ethoxycycloheptatriene with a mixture of iodine azide and sodium azide have been studied; cis-bicyclo[6,1,0]nonatriene gave a diazide, but trans-7,8-dibromobicyclo[4,2,0]octa-2,4-diene, and 5-ethoxybicyclo[3,2,0]hepta-2,6-diene gave β-iodo-azides as normal adducts. The structures of these adducts were elucidated from the spectra of the triazolyl derivatives prepared by reactions with dimethyl acetylenedicarboxylate.