Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide−Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation
Тип публикации: Journal Article
Дата публикации: 1997-05-01
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Краткое описание
The mechanism of 2-phenylbenzoxazole formation from benzoic acid and o-aminophenol in polyphosphoric acid (PPA) is studied by NMR spectroscopy and chemical analysis. Benzoic acid reacts with PPA to form benzoic−phosphoric anhydride and benzoic−polyphosphoric anhydride. The ratio of mixed anhydride to free carboxylic acid increases dramatically as the P2O5 content of PPA increases, but this ratio is independent of reaction temperature and time. When o-aminophenol dissolves in PPA, part of the hydroxyl group is converted to phosphate ester, and only protonated amine is detected. Benzoic acid, mixed anhydride, and PPA are in dynamic equilibrium, and so are PPA, o-aminophenol, and its phosphate ester. The mixed anhydride and o-aminophenol react to form 2-aminophenyl benzoate as the first reaction intermediate which undergoes rapid acyl migration to generate 2-hydroxybenzanilide. Ring closure of 2-hydroxybenzanilide to form 2-phenylbenzoxazole is acid catalyzed. The reactive components in phosphorus pentoxide−...
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So Y., Heeschen J. P. Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide−Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation // Journal of Organic Chemistry. 1997. Vol. 62. No. 11. pp. 3552-3561.
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So Y., Heeschen J. P. Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide−Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation // Journal of Organic Chemistry. 1997. Vol. 62. No. 11. pp. 3552-3561.
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TY - JOUR
DO - 10.1021/jo960441u
UR - https://doi.org/10.1021/jo960441u
TI - Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide−Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation
T2 - Journal of Organic Chemistry
AU - So, Ying-Hung
AU - Heeschen, Jerry P
PY - 1997
DA - 1997/05/01
PB - American Chemical Society (ACS)
SP - 3552-3561
IS - 11
VL - 62
SN - 0022-3263
SN - 1520-6904
ER -
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@article{1997_So,
author = {Ying-Hung So and Jerry P Heeschen},
title = {Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide−Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation},
journal = {Journal of Organic Chemistry},
year = {1997},
volume = {62},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jo960441u},
number = {11},
pages = {3552--3561},
doi = {10.1021/jo960441u}
}
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MLA
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So, Ying-Hung, and Jerry P Heeschen. “Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide−Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation.” Journal of Organic Chemistry, vol. 62, no. 11, May. 1997, pp. 3552-3561. https://doi.org/10.1021/jo960441u.
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