Premium
Concurrent formation of five and eight‐membered heterocyclic methylphosphonates in cyclization reactions from diethyleneglycole
Author(s) -
Moghimi Abolghasem,
Rafiei Javad,
Baghaie Parvin,
Aghabeygi Shokoofeh,
Moosavi S. Mojtaba
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.155
Subject(s) - chemistry , bifunctional , dimethyl methylphosphonate , ether , nucleophile , ring (chemistry) , medicinal chemistry , nuclear magnetic resonance spectroscopy , intramolecular force , polymer chemistry , organic chemistry , catalysis
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 MeP(O)(X)OCH 2 CH 2 OCH 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).