One-pot synthesis of symmetric 1,7-dicarbonyl compounds via a tandem radical addition–elimination–addition reaction?

RSC Advances Pub Date: 2013-06-26 DOI: 10.1039/C3RA42932F

Abstract

A novel approach to synthesize symmetric 1,7-dicarbonyl compounds via a tandem radical addition–elimination–addition reaction of S-carbonylmethyl xanthates with allylmethylsulfone and its analogues has been developed. Radicals were produced from S-carbonylmethyl xanthates by adding dilauroyl peroxide and reacted with allylmethylsulfone or analogues to generate terminal olefins as intermediates. The excessive radicals reacted with the intermediate olefins immediately to give adducts of symmetric 1,7-dicarbonyl compounds. This is an efficient method to synthesize 1,7-dicarbonyl compounds under mild conditions.

Graphical abstract: One-pot synthesis of symmetric 1,7-dicarbonyl compounds via a tandem radical addition–elimination–addition reaction
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