
TY  - JOUR
A1  - Paddon-Row, MN 
A1  - Hartcher, R 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1980
VL  - 33
IS  - 4
SP  - 785
EP  - 794
KW  - 
UR  - https://doi.org/10.1071/CH9800785 
N2  - 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. 
ER  -

