Of phosphine and primary or secondary phosphines

Addition of compounds containing P-H bonds a. Addition of phosphine and primary or secondary phosphines 

Well-tested laboratory directions for the preparation of the hydroxymethyl compound have been provided by Reeves and his co-workers.8 

It follows further that primary, secondary, and tertiary phosphines give -hydroxy phosphonium salts analogously 74-77 only in the absence of acid are tertiary phosphines obtained.75,78 

Bis(hydroxymethyl)diphenyl hosphonium chloride 77 To a solution of concentrated hydrochloric acid (100 ml) in tetrahydrofuran (200 ml) under nitrogen at room temperature are 

On treatment with aqueous or alcoholic alkali hydroxide or with tertiary amines the quaternary (hydroxymethyl)phosphonium salts are cleaved with loss of one equivalent of formaldehyde and formation of the tertiary phosphine 74-77 79,80 if the phosphonium salt contains more than one hydroxymethyl group, the amount of base used must not exceed one equivalent the fission occurs more easily the less basic is the resulting phosphine.75 As the tertiary (hydroxymethyl)phosphine quaternizes again with alkyl halides, any desired tertiary phosphine can be built up by successive quaternizations and basic fissions.75,77,79 

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