The Synthesis of bis-(2-Chloroethyl)-Methane Phosphonates

Woodnutt, David John (1993). The Synthesis of bis-(2-Chloroethyl)-Methane Phosphonates. MPhil thesis The Open University.



This thesis describes attempts to synthesise phosphoryl carbon mustards (bischloroethylphosphonates). Several strategies were employed based on phosphorus-carbon or carbon-carbon bond disconnections. Thus routes involving the reaction between:

(i) phosphites, nucleophilic phosphorus reagents, and haloalkanes or ketones;

(ii) dialkyl chlorophosphates, as electrophilic phosphorus reagents, and carbon nucleophiles; and

(iii) nucleophilic dialkyl alkanephosphonate anions and carbon electrophiles are described.

Thus far none of these routes yielded the desired compounds and some reasons for this are discussed.

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