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Radical addition reactions of phosphorus hydrides: Tuning the reactivity of phosphorus hydrides, the use of microwaves and Horner-Wadsworth-Emmons-type reactions

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JournalEuropean Journal of Organic Chemistry
DatePublished - 13 Mar 2006
Issue number6
Number of pages8
Pages (from-to)1547-1554
Original languageEnglish

Abstract

The reactivity of phosphorus hydrides in radical addition reactions are compared, and the substituents on phosphorus are shown to affect the efficiency of the reactions. The change in reactivity is attributed to the different bond dissociation energies of the P-H bonds, which have been calculated. Phosphorus hydrides with particularly weak P-H bonds are shown to undergo radical additions by microwave irradiation, in the absence of conventional initiators. These radical addition reactions produce phosphonothioates, phosphinothioates and phosphane sulfides, which react in HWE-type reactions, to afford substituted alkenes. (c) Wiley-VCH Verlag GmbH & Co.

    Research areas

  • radical reactions, heterocycles, synthetic methods, cyclisation, STEREOSELECTIVE-SYNTHESIS, HYPOPHOSPHOROUS ACID, EFFICIENT SYNTHESIS, H-PHOSPHONATE, CYCLIZATION, HYDROGEN, ESTERS, WATER, PHOSPHONOTHIOATES, REDUCTION

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