
%0 Journal Article
%A Byrne, LT 
%A Rye, AR 
%A Wege, D 
%T Diels-Alder additions of hexachlorocyclopentadiene to some 7-substituted norbornadienes
%J Australian Journal of Chemistry
%D 1974/09/01
%V 27
%N 9
%P 1961-1969
%K 
%R https://doi.org/10.1071/CH9741961
%U https://www.publish.csiro.au/paper/CH9741961 
%X In contrast to the normal addition mode of hexachlorocyclopentadiene (3) to norbornadiene, which yields mainly (but not exclusively) aldrin having the endo-exo-1,4:5,8-dimethanonaphthalene skeleton, the reaction of (3) with norbornadien-7-yl acetate gives three adducts: 1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-endo-endo-1,4:5,8-dimethanonaphthalen-syn-9-yl and -anti-9-yl acetates [(7) and (9)] and the 'normal' 1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-endo-exo-1,4:5,8-dimethanonaphthalen-syn-9-yl acetate (11). The addition of (3) to 7-t-butoxynorbornadiene yields mainly the anti-9-t-butoxy-endo-endo adduct, analogous to (9), while the addition of (3) to 7-methylnorbornadiene gives mainly syn-9-methyl-endo-exo-adduct,analogous to (11). The structure of these adducts has been determined by spectroscopic (N.M.R. and infrared) and chemical (photochemicalcyclization of the endo-endo systems) means. 
