Journal of the Chemical Society. Perkin transactions I p. 1501 - 1509 (1981)
Update date:2022-08-04
Topics:
Barrett, Anthony G. M.
Godfrey, Christopher R. A.
Hollinshead, David M.
Prokopiou, Panayiotis A.
Barton, Derek H. R.
et al.
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.
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