17132-01-3Relevant articles and documents
A Facile Method for the Reductive Deoxygenation of Aliphatic Oxygen-Functionalized Compounds
Hansson, Lars,Carlson, Rolf
, p. 103 - 107 (2007/10/02)
A one-pot three-step sequence for the reductive removal of oxygen from aliphatic carboxylic acids, ketones, aldehydes and alcohols to yield alkanes or alkyl groups has been developed.This was achieved by reducing the substrates to the alcohol level with lithium aluminium hydride followed by in situ preparation of the corresponding alkyl sulfate which is finally treated with a second portion of lithium aluminium hydride.Yields as determined by gas liquid chromatography were in the range 89-99percent.Preparative experiments with 1-decanol and decanoic acid afforded 92 and 81percent yield, respectively, of distilled decane.The effect of various additives on the yield of the reaction is reported.Improvement of a recently reported method for the conversion of 1,4a-dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one into r-1,t-4a-dimethylperhydronaphthalen-c-8a-ol and some observations concerning the reduction of cholesterol are also discussed.
PHOTOREDUCTION DES ESTERS CARBOXYLIQUES DANS L'HEXAMETHYLPHOSPHORTRIAMIDE (HMPT)
Portella, C.,Deshayes, H.,Pete, J. P.,Scholler, D.
, p. 3635 - 3644 (2007/10/02)
Use of HMPT as solvent in photochemistry allows efficient photoreductions.Alkyl esters and especially non absorbing alkyl acetates are photoreduced in excellent yields into alkanes.In the latter case, a protonating agent is necessary.Numerous examples illustrate the generality and convenience of the reaction.This photoreduction involves an electron transfer from HMPT to ester.
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 (2007/10/02)
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.