AGENTS OF THE G SERIES STUDIES IN THE CHEMISTRY OF ORGANOPHOSPHORUS COMPOUNDS
Memorandum rept. no. 2
CHEMICAL CORPS ARMY CHEMICAL CENTER MD
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Trivalent P compounds containing at least one P-cl bond are incapable of reacting with electrophilic reagents, such as alkyl halides, due to the positive nature of the P atoms. Alcoholysis of triethyl phosphate with butyl alcohol using sodium butoxide as catalyst results in the formation of mixed butyl ethyl phosphates and butyl ethyl ether. This phenomenon can be explained by assuming a ten-electron intermediate between the nucleophilic reagent, butoxy ion, and triethyl phosphate with subsequest decomposition of the complex to the observed products. The concept is strengthened by the fact that diethyl ether is also formed in this reaction. Alkylation of amines by alkyl phosphates can also be accounted for by the assumption of the existence of a complex between tri-ethyl phosphate and a primary or secondary amine. Results of the alkylation studies make it appear that the rearrangement of dimethyl hydrogen phosphite follows a similar course of self-alkylation as is exhabited by the alkylation of amines and alkoxides by triethyl phosphate. This theory requires that dimethyl hydrogen phosphite is an equilibrium mixture of the trivalent and pentavalent forms.
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