
%0 Journal Article
%A Collins, DJ 
%A Molinski, TF 
%A Sjovall, J 
%T The stability of allylic and vinylic deuterium atoms during the lithium/ammonia reduction of some styrenoid systems
%J Australian Journal of Chemistry
%D 1983/02/01
%V 36
%N 2
%P 361-370
%K 
%R https://doi.org/10.1071/CH9830361
%U https://www.publish.csiro.au/paper/CH9830361 
%X Reduction of 2-(p-methoxyphenyl)cyclohexan-1-one (8) with lithium aluminium deuteride followed by acetylation gave trans-l-acetoxy-2-(p-methoxyphenyl)(1-2H1)cycohexane (10b). Base-catalysed deuteration of 2-(p-methoxypheny1)cyclohexan-1-one (8) afforded the corresponding trideuterated ketone (11a) which upon hydride reduction and acetylation yielded trans-1-acetoxy-2-(p-methoxy- phenyl)(2,6,6-2H3)cyclohexane (15b). Pyrolysis of the acetate (10b) at 600º/1.0 mm gave 1-(p-methoxyphenyl)(2-2H1)cyclohex-1-ene (16) which was separated from the unconjugated isomer (13) by preparative g.l.c. 1-(p-Methoxyphenyl)(3,3-2H2)cyclohex-1-ene (18) was similarly obtained by pyrolysis of the trideutero acetate (15b). Lithium/ammonia reduction of the deuterated styrenoid compounds (16) and (18) proceeded in each case without any detectable loss or redistribution of the deuterium atoms. 
