
%0 Journal Article
%A Serelis, AK 
%A Solomon, DH 
%A Steel, PJ 
%T Stereospecificity in the Geminate Recombination of 1,3-Diphenylpropyl Radical Pairs
%J Australian Journal of Chemistry
%D 1989/03/01
%V 42
%N 3
%P 395-404
%K 
%R https://doi.org/10.1071/CH9890395
%U https://www.publish.csiro.au/paper/CH9890395 
%X 1,3,4,6-Tetraphenylhexanes (3m) and (3r), formed by the geminate recombination of 1,3- diphenylpropyl (1) radical pairs generated at 90º from diastereomerically pure meso - and rac-1,1&#8242;,3,3'-tetraphenylazopropane (2m) and (2r), are obtained with substantial retention (up to 46% d.e .) of precursor stereochemistry. The stable nitroxyls 1,1,3,3-tetramethylisoindolin-2-yloxyl (4) and 2,2,6,6-tetramethylpiperidin-1-yloxyl (5) were used as scavengers to isolate the geminate reaction (30-35% cage effect). A slight selectivity (64% d.e .) in favour of meso-l,3,4,6-tetraphenylhexane (3m) is found in the encounter reaction of (1). The nature of the molecular motions associated with the partial loss of stereochemistry during the reaction (2) &#8594; (1) &#8594;(3) is discussed. n.m.r. spectroscopy, particularly 13C, was used for correlating product and precursor stereochemistries and for diastereomer identification. The structural assignments were confirmed by single-crystal X-ray diffraction analysis of (3r). 
