
TY  - JOUR
A1  - Collins, DJ 
A1  - Molinski, TF 
A1  - Sjovall, J 
T1  - The stability of allylic and vinylic deuterium atoms during the lithium/ammonia reduction of some styrenoid systems
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1983
VL  - 36
IS  - 2
SP  - 361
EP  - 370
KW  - 
UR  - https://doi.org/10.1071/CH9830361 
N2  - 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. 
ER  -

