On the reactions between phosphorus pentachloride and lactones

Article abstract of DOI:10.1080/10426509908037028

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.

Full text of DOI:10.1080/10426509908037028

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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ON THE REACTIONS BETWEEN
PHOSPHORUS PENTACHLORIDE
AND LACTONES
a
b
Valeh Mehralioğlu Ismaili , Adnan Aydin & M. M.
a
Kantaeva
a
Baku State University , Baku, 370146, Azerbaijan
b
Marmara University, Faculty of Science and
Letters, Department of Chemisty , Göztepe,
Istanbul, Turkey
Published online: 24 Sep 2006.
To cite this article: Valeh Mehralioğlu Ismaili , Adnan Aydin & M. M. Kantaeva
(
1999) ON THE REACTIONS BETWEEN PHOSPHORUS PENTACHLORIDE AND LACTONES,
Phosphorus, Sulfur, and Silicon and the Related Elements, 149:1, 137-142, DOI:
0.1080/10426509908037028
1
To link to this article: http://dx.doi.org/10.1080/10426509908037028
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