4939-91-7Relevant academic research and scientific papers
The Chemical and Electrochemical Reductions of 5-Bromodecalone and 4-Bromodecalone
Hamon, David P. G.,Richards, Kenneth R.
, p. 2243 - 2259 (2007/10/02)
5-Bromodecalone (1) was prepared by the reaction of potassium bromide in acetonitrile on (4aα,5α,8aβ)-5-tosyloxyoctahydronaphthalen-1(2H)-one (15) with apparent retention of configuration.It was also prepared by hydrogen bromide cleavage of (3aRS,3bRS,7aRS)-octahydro-7H-cyclopentacyclopropabenzen-7-one (17).On reaction with sodium potassium alloy ketone (1) gives α-decalone (33) and ketone (17) as the principal products whereas reduction with tributylstannane gives only ketone (33).Electrochemical reduction of ketone (1) gives trans-cyclodec-5-en-1-one (3) as well as ketones (17) and (33). 4-Bromodecalone (2) was prepared from (4α,4aα,8aβ)-4-tosyloxyoctahydronaphthalen-1(2H)-one (29), by the reaction with potassium bromide in acetonitrile, with inversion of configuration.Electrochemical reduction of ketone (2) gives trans-1-acetyl-2-vinylcyclohexane (36), α-decalone (33), (E)-cyclodec-4-en-1-one (4) and (1aRS,1bSR,5aRS,6aRS)-octahydrocyclopropainden-6(6aH)-one (24).
