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The synthesis of hydroxy‐methylenebisphosphonates (2a–c) by the addition of dialkyl phosphite to the carbonyl group of the corresponding α‐oxophosphonate (1a–c) was studied under microwave irradiation (MW) and solventless conditions in the presence of dialkylamine as the catalyst. After optimization, products 2a and 2b were obtained selectively and in good yields avoiding the formation of the phosphonate‐phosphate by‐product (3a and 3b) that is the result of a rearrangement. The MW‐assisted synthesis of hydroxybisphosphonates (2a and 2b) offers complete conversions and a chemoselectivity of 100% as compared to the not so efficient thermal reaction. At the same time, the phenyl‐substituted methylenebisphosphonate 2c could be obtained in only 75% selectivity. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:350–354, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20558
Heteroatom Chemistry – Wiley
Published: Jan 1, 2009
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