Journal of Organic Chemistry, volume 76, issue 18, pages 7431-7437
Exploring the synthetic versatility of the Lewis acid induced decomposition reaction of α-diazo-β-hydroxy esters. The case of ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate.
Publication type: Journal Article
Publication date: 2011-08-17
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate was prepared by aldol-type condensation of ethyl diazoacetate with isatin. A systematic and mechanistic study on the Lewis acid induced decomposition reaction of this valuable diazo precursor was carried out with the aim to gain new insights into the mechanistic aspects of the reaction as well as to further understand the factors and experimental conditions which affect the relative product distribution. The reaction, which may proceed via cationic and noncationic mechanisms, was found to be significantly influenced by the reaction environment determined by the characteristics of the Lewis acid employed, by the ability of the Lewis acid to form a complex with the alcohol functionality of the α-diazo-β-hydroxy ester, and by the polarity and nucleophilicity of the solvent used.
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- We do not take into account publications that without a DOI.
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Gioiello A. et al. Exploring the synthetic versatility of the Lewis acid induced decomposition reaction of α-diazo-β-hydroxy esters. The case of ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate. // Journal of Organic Chemistry. 2011. Vol. 76. No. 18. pp. 7431-7437.
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Gioiello A., Venturoni F., Marinozzi M., Natalini B., Pellicciari R. Exploring the synthetic versatility of the Lewis acid induced decomposition reaction of α-diazo-β-hydroxy esters. The case of ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate. // Journal of Organic Chemistry. 2011. Vol. 76. No. 18. pp. 7431-7437.
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TY - JOUR
DO - 10.1021/jo201205u
UR - https://doi.org/10.1021%2Fjo201205u
TI - Exploring the synthetic versatility of the Lewis acid induced decomposition reaction of α-diazo-β-hydroxy esters. The case of ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate.
T2 - Journal of Organic Chemistry
AU - Venturoni, Francesco
AU - Pellicciari, Roberto
AU - Gioiello, Antimo
AU - Marinozzi, Maura
AU - Natalini, Benedetto
PY - 2011
DA - 2011/08/17 00:00:00
PB - American Chemical Society (ACS)
SP - 7431-7437
IS - 18
VL - 76
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2011_Gioiello,
author = {Francesco Venturoni and Roberto Pellicciari and Antimo Gioiello and Maura Marinozzi and Benedetto Natalini},
title = {Exploring the synthetic versatility of the Lewis acid induced decomposition reaction of α-diazo-β-hydroxy esters. The case of ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate.},
journal = {Journal of Organic Chemistry},
year = {2011},
volume = {76},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021%2Fjo201205u},
number = {18},
pages = {7431--7437},
doi = {10.1021/jo201205u}
}
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MLA
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Gioiello, Antimo, et al. “Exploring the synthetic versatility of the Lewis acid induced decomposition reaction of α-diazo-β-hydroxy esters. The case of ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate..” Journal of Organic Chemistry, vol. 76, no. 18, Aug. 2011, pp. 7431-7437. https://doi.org/10.1021%2Fjo201205u.