Unexpected stoichiometry in the cleavage of bis(4-nitrophenyl) phosphate and 4-nitrophenyl phosphorochloridate by alkaline hydrogen peroxide
Publication type: Journal Article
Publication date: 2000-01-01
scimago Q3
wos Q3
SJR: 0.318
CiteScore: 4.1
Impact factor: 1.8
ISSN: 08943230, 10991395
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Reaction of alkaline hydrogen peroxide with bis(4-nitrophenyl) phosphate ion proceeds with simultaneous liberation of ca 2 equiv. of 4-nitrophenol per mole of substrate, and no evidence for build-up of an intermediate. Reaction of HO2− with the more activated 4-nitrophenyl phosphorochloridate gives 4-nitrophenol in up to 40% yield with simple first-order kinetics and no indication of a long-lived intermediate. A fast intramolecular nucleophilic displacement of 4-nitrophenolate ion by peroxide in the initially formed 4-nitrophenyl peroxophosphate is proposed to explain this behavior. Copyright © 2000 John Wiley & Sons, Ltd.
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Meja Radillo Y. et al. Unexpected stoichiometry in the cleavage of bis(4-nitrophenyl) phosphate and 4-nitrophenyl phosphorochloridate by alkaline hydrogen peroxide // Journal of Physical Organic Chemistry. 2000. Vol. 13. No. 9. pp. 505-510.
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Meja Radillo Y., Yatsimirsky A. K., Foroudian H. J., Gillitt N. D., Bunton C. A. Unexpected stoichiometry in the cleavage of bis(4-nitrophenyl) phosphate and 4-nitrophenyl phosphorochloridate by alkaline hydrogen peroxide // Journal of Physical Organic Chemistry. 2000. Vol. 13. No. 9. pp. 505-510.
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TY - JOUR
DO - 10.1002/1099-1395(200009)13:9<505::AID-POC277>3.0.CO;2-N
UR - https://doi.org/10.1002/1099-1395(200009)13:9<505::AID-POC277>3.0.CO;2-N
TI - Unexpected stoichiometry in the cleavage of bis(4-nitrophenyl) phosphate and 4-nitrophenyl phosphorochloridate by alkaline hydrogen peroxide
T2 - Journal of Physical Organic Chemistry
AU - Meja Radillo, Yamilet
AU - Yatsimirsky, Anatoly K.
AU - Foroudian, Houshang J.
AU - Gillitt, Nicholas D.
AU - Bunton, Clifford A.
PY - 2000
DA - 2000/01/01
PB - Wiley
SP - 505-510
IS - 9
VL - 13
SN - 0894-3230
SN - 1099-1395
ER -
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BibTex (up to 50 authors)
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@article{2000_Meja Radillo,
author = {Yamilet Meja Radillo and Anatoly K. Yatsimirsky and Houshang J. Foroudian and Nicholas D. Gillitt and Clifford A. Bunton},
title = {Unexpected stoichiometry in the cleavage of bis(4-nitrophenyl) phosphate and 4-nitrophenyl phosphorochloridate by alkaline hydrogen peroxide},
journal = {Journal of Physical Organic Chemistry},
year = {2000},
volume = {13},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/1099-1395(200009)13:9<505::AID-POC277>3.0.CO;2-N},
number = {9},
pages = {505--510},
doi = {10.1002/1099-1395(200009)13:9<505::AID-POC277>3.0.CO;2-N}
}
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MLA
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Meja Radillo, Yamilet, et al. “Unexpected stoichiometry in the cleavage of bis(4-nitrophenyl) phosphate and 4-nitrophenyl phosphorochloridate by alkaline hydrogen peroxide.” Journal of Physical Organic Chemistry, vol. 13, no. 9, Jan. 2000, pp. 505-510. https://doi.org/10.1002/1099-1395(200009)13:9<505::AID-POC277>3.0.CO;2-N.