Phosphorus, Sulfur and Silicon and the Related Elements p. 137 - 142 (1999)
Update date:2022-08-17
Topics:
Ismaili, Valeh Mehralioglu
Aydin, Adnan
Kantaeva
Reactions between PCl5 and substituted or unsubstituted β-, γ- and ε-lactones have been investigated. Although γ-butyrolactone substituted at α-position with an alkyl radical has given phosphorylated products of both cyclic ethers and chlorinated carboxylic acid chlorides along with γ-chlorobutanoic acid chloride, halogen substituted γ-butyrolactone such as α-bromo-γ-butyrolactone yielded α-bromo-γ-chlorobutanoic acid chloride in similar manner with β-propiolactone which gives β-chloropropionic acid chloride. The nature of radicals present at γ-position also affects the reaction products. Methyl or heptyl radicals yielded different products; in the latter case phosphorylated products were not isolated. The reaction pathway of ε-caprolactone with PCl5 is changed by the temperature of the reaction mixture. It reacts at 20-30°C to give α,α-dichlorooxepane and ε-chlorohexanoic acid chloride, while a phosphorylated product was observed at 60-70°C. Possible mechanisms of these reactions are discussed.
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