
TY  - JOUR
A1  - Lambert, JD 
A1  - Porter, QN 
T1  - Vinylindenes and some heteroanalogues in the Diels-Alder reaction. VIII. 1-Benzyl-3-vinylindole as a diene
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1981
VL  - 34
IS  - 7
SP  - 1483
EP  - 1490
KW  - 
UR  - https://doi.org/10.1071/CH9811483 
N2  - 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. 
ER  -

