79677-00-2Relevant academic research and scientific papers
Dissolving Metal Reduction of Esters to Alkanes. A Method for the Deoxygenation of Alcohols
Barrett, Anthony G. M.,Godfrey, Christopher R. A.,Hollinshead, David M.,Prokopiou, Panayiotis A.,Barton, Derek H. R.,et al.
, p. 1501 - 1509 (1981)
Divers carboxylic esters have been reduced with dissolving Group 1A metals.Using lithium in ethylamine, sterically hindered esters (RCO2R') were deoxygenated giving the alkane (R'H) whereas non-hindered esters regenerated the parent alcohol (R'OH).This permitted the selective deoxygenation of diesters.Conversely, potassium-sodium eutectic solubilised with 18-crown-6 in t-butylamine and tetrahydrofuran (THF) efficiently deoxygenated both hindered and non-hindered esters.In the absence of nucleophiles at ambient temperture the principal reaction of carboxylic ester radical anions was deoxygenation.
