α-Hydroxyphosphonates as intermediates in the Kabachnik–Fields reaction: New proof of their reversible formation
Publication type: Journal Article
Publication date: 2020-06-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The rearrangement of dimethyl α-hydroxybenzylphosphonate to the corresponding benzylphosphate in the presence of an alkali carbonate in acetone under phase transfer catalytic conditions was accompanied by the formation of dimethyl α–hydroxyisopropylphosphonate, proving the reversibility of the formation of the hydroxyphosphonate from benzaldehyde and dimethyl phosphite in the Pudovik reaction. The dimethyl phosphite formed in situ from the adduct under the conditions of the rearrangement reaction was trapped by acetone.
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Keglevich G., Rádai Z. α-Hydroxyphosphonates as intermediates in the Kabachnik–Fields reaction: New proof of their reversible formation // Tetrahedron Letters. 2020. Vol. 61. No. 23. p. 151961.
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Keglevich G., Rádai Z. α-Hydroxyphosphonates as intermediates in the Kabachnik–Fields reaction: New proof of their reversible formation // Tetrahedron Letters. 2020. Vol. 61. No. 23. p. 151961.
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TY - JOUR
DO - 10.1016/j.tetlet.2020.151961
UR - https://doi.org/10.1016/j.tetlet.2020.151961
TI - α-Hydroxyphosphonates as intermediates in the Kabachnik–Fields reaction: New proof of their reversible formation
T2 - Tetrahedron Letters
AU - Keglevich, György
AU - Rádai, Zita
PY - 2020
DA - 2020/06/01
PB - Elsevier
SP - 151961
IS - 23
VL - 61
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2020_Keglevich,
author = {György Keglevich and Zita Rádai},
title = {α-Hydroxyphosphonates as intermediates in the Kabachnik–Fields reaction: New proof of their reversible formation},
journal = {Tetrahedron Letters},
year = {2020},
volume = {61},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/j.tetlet.2020.151961},
number = {23},
pages = {151961},
doi = {10.1016/j.tetlet.2020.151961}
}
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MLA
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Keglevich, György, and Zita Rádai. “α-Hydroxyphosphonates as intermediates in the Kabachnik–Fields reaction: New proof of their reversible formation.” Tetrahedron Letters, vol. 61, no. 23, Jun. 2020, p. 151961. https://doi.org/10.1016/j.tetlet.2020.151961.