Issue 7, 1988

Magnesium- and titanium-induced reductive coupling of carbonyl compounds: efficient syntheses of pinacols and alkenes

Abstract

Finely dispersed magnesium on graphite was found to be a totally selective single-electron transfer reagent of general utility for the reduction of various kinds of carbonyl and dicarbonyl compounds to pinacols, a reaction quite compatible with a number of functional groups. Similarly, titanium on graphite proved to be a universally applicable reducing agent for the efficient conversion of pinacols, carbonyl and dicarbonyl compounds into alkenes and cycloalkenes respectively and for the cyclization of oxo alkanoates to enol ethers, facilitating and unifying the highly useful McMurry reaction. The practicability of the presently known carbonyl coupling methods is discussed in the light of these results.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 1729-1734

Magnesium- and titanium-induced reductive coupling of carbonyl compounds: efficient syntheses of pinacols and alkenes

A. Fürstner, R. Csuk, C. Rohrer and H. Weidmann, J. Chem. Soc., Perkin Trans. 1, 1988, 1729 DOI: 10.1039/P19880001729

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