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Radical reaction of sodium hypophosphite with terminal alkynes: synthesis of 1,1-bis-H-phosphinates.

ABSTRACT: [reaction: see text] The room-temperature radical addition of sodium hypophosphite to terminal alkynes produces the previously unknown 1-alkyl-1,1-bis-H-phosphinates in moderate yield. The reaction is initiated by R3B and air and proceeds under mild conditions in an open container. The bissodium salts precipitate spontaneously from the reaction mixtures, thus providing a simple purification procedure and the opportunity for multigram synthesis. The 1,1-bis-H-phosphinate products are novel precursors of the biologically important 1,1-bisphosphonates.

SUBMITTER: Gouault-Bironneau S

PROVIDER: S-EPMC2531071 | biostudies-literature | 2005 Dec

REPOSITORIES: biostudies-literature

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Radical reaction of sodium hypophosphite with terminal alkynes: synthesis of 1,1-bis-H-phosphinates.

Gouault-Bironneau Sonia S Deprèle Sylvine S Sutor Amber A Montchamp Jean-Luc JL

Organic letters 20051201 26

[reaction: see text] The room-temperature radical addition of sodium hypophosphite to terminal alkynes produces the previously unknown 1-alkyl-1,1-bis-H-phosphinates in moderate yield. The reaction is initiated by R3B and air and proceeds under mild conditions in an open container. The bissodium salts precipitate spontaneously from the reaction mixtures, thus providing a simple purification procedure and the opportunity for multigram synthesis. The 1,1-bis-H-phosphinate products are novel precur ...[more]

PMID: 16354097

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