Other compounds related to the phosphorofluoridates

Reference has already been made to some of these compounds in the previous section and a description of these and of otha related substances is now given. 

Potassium thiocyanate reacted readily with diethyl phoe-phorochloridate giving diethyl phosphorothiocyanidate, 

Gaseous ammonia reacted with the phosphorochloridate at 0° producing solid diethyl phosphoramidate in accordance with the equation Et,PO,a+2NH, = Et,POjNH,+NH,ci. 

In a similar manner, gaseous methylamine gave diethjd methylphosphoramidate, EtaPOgNHMe, which was, howevCT, Saunders, Stacey, Wild and Wilding, J. Chem. Soc. 1948, p. 699. 

It was important to determine whether the fluorine atom must be attached directly to the phosphorus atom in order to I oduce phosphorofluoridate-like activity. For this purpose we treated the toxic di-sec.-butyl phosphorofluoridate with diazomethane and obtained a compound which was undoubtedly di ec. butyl fluoromethylphosphonate (XIX). Unlike the parent phosphorofluoridate, the fluoromethylphosphonate was only slightly toxic and produced neghgible myosis. (It may be mentioned here that thionyl chloride and carbonyl chloride were converted by means of diazomethane into bis (chloromethyl)-sulphoxide and /S dichloroacetone respectively.) 

Potassium thiocyanate reacted readily with diethyl phos-phorochloridate giving diethyl phosphorothiocyanidate, Et OjCl + KSCN = EtjPO CN + KQ. 

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