An efficient method for the phosphonation of C=X compounds |
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| Authors: | A O Kolodyazhnaya O O Kolodyazhnaya O I Kolodyazhnyi |
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| Institution: | (1) Department of Comparative Biosciences, Division of Pharmaceutical Sciences, and Center for Molecular and Environmental Toxicology, University of Wisconsin, Madison, Wisconsin, USA |
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| Abstract: | Reaction of trialkyl phosphites with C=X electrophiles (aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates,
isothiocyanates, and activated olefins) in the presence of amines and anilines hydrohalides was studied. We found that pyridine
hydrohalides effectively activate the reaction of tralkyl phosphites with various C=X electrophiles: aldehydes, ketones, ketophosphonates,
aldimines, ketimines, isocyanates, isothiocyanates, and activated olefins. Particularly high activity showed pyridine hydroiodide.
This reaction is a convenient method of synthesis of hydroxyphosphonates, aminophosphonates, carbamoylphosphonates, carbamoylthiophosphonates,
and methylenebisphosphonates. |
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