
%0 Journal Article
%A Paddon-Row, MN 
%A Hartcher, R 
%T Orbital interactions. VIII. Competition kinetic measurements of the Birch reduction of some compounds having the bicyclo[2,2,1]heptadiene framework as a means of investigating orbital interactions through space in these systems
%J Australian Journal of Chemistry
%D 1980/04/01
%V 33
%N 4
%P 785-794
%K 
%R https://doi.org/10.1071/CH9800785
%U https://www.publish.csiro.au/paper/CH9800785 
%X Relative rate constants for the Birch reduction (Li/liq. NH3/t-butyl alcohol) of norbornadiene (1),1,4-dihydro-1,4-methanonaphthalene (3), 9-(1-methylethylidene)-1,4-dihydro-1,4-methanonaphthalene(5), 1,4- dihydro-1,4-epoxynaphthalene (7), lithium benzoate, &#945;-methylstyrene, and the hexahydrobenzenomethanoanthracene(20a), were obtained and compared with that obtained for the reduction of norbornene from an earlier study. Compounds (1), (3) and (5) were some 105 times more readily reduced than norbornene. These results are best explained in terms of the presence of through-space interactions operating between the two lowest unoccupied molecular orbitals in these molecules. The Birch reduction of (7) gave mainly 1,4-dihydronaphthalene (17).A mechanism for this reaction is presented. 
