Tetrahedron

Organic chemistry in water (part v) Nucleophilic addition of water-soluble phosphines on activated Alkynes: an efficient synthesis of new vinylphosphonium salts and …

C Larpent, G Meignan, H Patin

Index: Larpent, Chantal; Meignan, Gerard; Patin, Henri Tetrahedron, 1990 , vol. 46, # 18 p. 6381 - 6398

Full Text: HTML

Citation Number: 42

Abstract

Triphenylphosphinc m-trisulfonate [P (mC6H4S03Na) 3= TPPTS] 1 and triphenylphosphine m-monosulfonate [Ph2P (mC6H4SO3Na)= TPPMS] 2 react in water with activated alkynes RC s CA (A= CO2H, CO2Rl, COR2, CHO) affording new vinylphosphonium salts or vinylphosphine oxides or alkenes depending on the pH of the aqueous solution and on the nature of the substituent R. The reactions of 1 or 2 with alkynes bearing an electron- ...