
%0 Journal Article
%A Lambert, JD 
%A Porter, QN 
%T Vinylindenes and some heteroanalogues in the Diels-Alder reaction. VIII. 1-Benzyl-3-vinylindole as a diene
%J Australian Journal of Chemistry
%D 1981/07/01
%V 34
%N 7
%P 1483-1490
%K 
%R https://doi.org/10.1071/CH9811483
%U https://www.publish.csiro.au/paper/CH9811483 
%X 1-Benzyl-3-vinylindole gives stable adducts resulting from [2+4] cycloadditions with 1,4-benzo-quinone, 1,4-naphthoquinone, N- phenylmaleimide and maleic anhydride. Vicinal 1H n.m.r. coupling constants for protons on the cyclohexene rings are used to show that the first two adducts probably have half-chair conformations, while the last have boat conformations. Non-equivalence of the benzyl methylene protons of the benzoquinone adduct has been shown to display a surprising temperature dependence. The adduct of the vinylindole and ethenetetracarbonitrile is shown to be a cyclobutane resulting from a [2+2] cycloaddition. 
