Abstract
The reaction of sodium hydride with ω-hydroxyalkyltriphenylphosphonium salts Ph3P(CH2)nOH X–(I) has been investigated. The salt (I; n= 1, X = I) gave triphenylphosphine and formaldehyde. The salt (I; n= 2, X = I) gave triphenylphosphine oxide and ethylene. The salts (I; n= 4 or 5, X = I or Cl) could not be prepared. The salt (I; n= 6, X = I) gave mainly triphenylphosphine and hex-5-en-1-ol with some 6-hydroxyhexyldiphenylphosphine, 6-phenoxyhexyldiphenylphosphine, and 6-phenoxyhexylidenetriphenylphosphorane. The salt (I; n= 11, X = Br) gave 11-phenoxyundecyldiphenylphosphine, 11-hydroxyundecyldiphenylphosphine, and 11-phenoxyundecylidenetriphenylphosphorane. Sodium hydride with 2,3-dihydroxypropyltriphenylphosphonium iodide gave triphenylphosphine oxide and allyl alcohol.Similar reactions were carried out with ω-hydroxyalkyltriphenylarsonium salts, Ph3As(CH2)nOH X–(XIV). The salt (XIV; n= 6, X = I) gave triphenylarsine and hex-5-en-1-ol. The salt (XIV; n= 11, X = Br) gave mainly triphenylarsine and undec-10-en-1-ol.Similar reactions were carried out with ω-hydroxyalkyldimethylphenylammonium salts, Ph(Me)2N(CH2)nOH X–(XV). The salt (XV; n= 3, X = I) gave dimethylaniline and allyl alcohol. The salt (XV; n= 11, X = Br) gave 11-methoxyundecylmethylphenylamine.
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