Radical reaction of sodium hypophosphite with terminal alkynes: synthesis of 1,1-bis-H-phosphinates.
[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.
Gouault-Bironneau
Sonia
S
Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129, USA.
Deprèle
Sylvine
S
Sutor
Amber
A
Montchamp
Jean-Luc
JL
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010721:Phosphinic Acids / Q000737:chemistry*
D000480:Alkynes; D009943:Organophosphorus Compounds; D010721:Phosphinic Acids; C009287:sodium hypophosphite