Concurrent formation of five and eight-membered heterocyclic methylphosphonates in cyclization reactions from diethyleneglycole

✍ Scribed by Abolghasem Moghimi; Javad Rafiei; Parvin Baghaie; Shokoofeh Aghabeygi; S. Mojtaba Moosavi

• Book ID: 102341075
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2009
• Tongue: English
• Weight: 140 KB
• Volume: 46
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.155

✦ Synopsis

Abstract

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Two methodologies have been investigated for the preparation of heterocyclic methylphosphonate using diethyleneglycole and either MPDC or DMMP as the bifunctional group starting materials needed for cyclization reactions. In addition to the eight‐membered ring methylphosphonate I the five‐membered ring methylphosphonate II was unexpectedly found to be formed during the cyclization reactions. This small‐size cyclic methylphosphonate may have been generated from an intramolecular cyclization reaction by the nucleophilic attack of the ether oxygen atom of the intermediate MeP(O)(X)OCH~2~CH~2~OCH~2~CH~2~OH (X = Cl or OMe). The resulting cyclic phosphonates were purified and characterized by NMR and mass spectroscopy. J. Heterocyclic Chem., (2009).