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Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solventless conditions
Тип публикации: Journal Article
Дата публикации: 2009-11-06
scimago Q4
wos Q3
БС2
SJR: 0.146
CiteScore: 2.3
Impact factor: 1.4
ISSN: 10427163, 10981071
General Chemistry
Краткое описание
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
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Grün A. et al. Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solventless conditions // Heteroatom Chemistry. 2009. Vol. 20. No. 6. pp. 350-354.
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Grün A., Molnã¡r I. G., Bertã³k B., Greiner I., Keglevich G. Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solventless conditions // Heteroatom Chemistry. 2009. Vol. 20. No. 6. pp. 350-354.
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TY - JOUR
DO - 10.1002/hc.20558
UR - https://doi.org/10.1002/hc.20558
TI - Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solventless conditions
T2 - Heteroatom Chemistry
AU - Grün, Alajos
AU - Molnã¡r, Istvã¡n Gã¡bor
AU - Bertã³k, Bã©la
AU - Greiner, István
AU - Keglevich, György
PY - 2009
DA - 2009/11/06
PB - Wiley
SP - 350-354
IS - 6
VL - 20
SN - 1042-7163
SN - 1098-1071
ER -
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@article{2009_Grün,
author = {Alajos Grün and Istvã¡n Gã¡bor Molnã¡r and Bã©la Bertã³k and István Greiner and György Keglevich},
title = {Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solventless conditions},
journal = {Heteroatom Chemistry},
year = {2009},
volume = {20},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/hc.20558},
number = {6},
pages = {350--354},
doi = {10.1002/hc.20558}
}
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MLA
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Grün, Alajos, et al. “Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solventless conditions.” Heteroatom Chemistry, vol. 20, no. 6, Nov. 2009, pp. 350-354. https://doi.org/10.1002/hc.20558.