Primary alkyl iodides, phosphonate

Reaction with Primary Alkyl Bromides, Iodides, or Triflates. Treatment of the sodium or potassium salt of phenylsulfonylfluoromethylphosphonate with primary alkyl bromides (eq 6), iodides, or triflates (eq 7) affords (Q -fluoro-Q -phenylsulfonylalkyl)phosphonates in moderate to good yields, which could be converted to the corresponding (Q -fluoroalkyl)phosphonates via Na(Hg)-mediated desulfonation (eq7).l ... 

Primary, secondary and tertiary alkyl chlorides, bromides or iodides all undergo reaction (vinyl halides and alkyl fluorides do not), as do cycloalkyP" " and benzyP " halides. Apart from the compilation of examples by Kinnear and Perren ", other examples are spread very widely and rather thinly throughout the literature. Some isomerization is to be found when using certain alkyl halides for example, -propyl and -butyl halides afford the isopropyl- and (l-methylpropyl)-phosphonic dichlorides, and isobutyl chloride yields r r/-butylphosphonic dichloride ". Whilst Me3SiCH2Cl affords the expected phosphonic dichloride, neopentyl chloride yields (l,l-dimethylpropyl)phosphonic dichloride ". 1,5-Dichloropentane reacts but affords only (4-chloro-l-methylbutyl)phosphonic dichloride " ... 

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