
%0 Journal Article
%A Elix, JA 
%A Wilson, WS 
%A Warrener, RN 
%A Calder, IC 
%T A new synthesis of azocines
%J Australian Journal of Chemistry
%D 1972/04/01
%V 25
%N 4
%P 865-874
%K 
%R https://doi.org/10.1071/CH9720865
%U https://www.publish.csiro.au/paper/CH9720865 
%X Methyl and ethyl 7,8-diphenylazocine-2-carboxylate have been prepared by the reaction of dimethyl tricyclo[4,2,2,02,5]deca-3,7,9-triene-7,8-dicarboxylate with methyl or ethyl 5,6-diphenyl-1,2,4-triazine-3-carboxylate. The flexibility of this azocine ring system has been studied by p.m.r. spectroscopy and it was found that a higher temperature was required to effect rapid ring inversion in this case, in comparison with the related cyclooctatetraenes. A related bridged dihydroazocine (8) has been synthesized by the [&#960;2s + &#960;4s] cycloaddition of dimethyl tricyclo-[4,2,2,02,5]deca-3,9-diene-7,8-dicarboxylate to ethyl 5,6-diphenyl-1,2,4-triazine-3-car-boxylate. In contrast to previously described dihydroazocines, this compound exists entirely in the monocyclic form. Other [&#960;2s + &#960;4s] cycloadditions have also been described in which the &#960;4s component was part of a triazine or a 3-azabicyclo-[4,2,0]octa-2,4-diene ring system. 
