New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol
Тип публикации: Journal Article
Дата публикации: 2000-06-09
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
10891140
Organic Chemistry
Краткое описание
N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pK(a) values of these N-substituted aminophthalimides suggest that the success of the Mitsunobu reaction in this case seems to be governed more by steric than by electronic effects. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.
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Brosse N., Pinto M., Jamart-Grégoire B. New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol // Journal of Organic Chemistry. 2000. Vol. 65. No. 14. pp. 4370-4374.
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Brosse N., Pinto M., Jamart-Grégoire B. New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol // Journal of Organic Chemistry. 2000. Vol. 65. No. 14. pp. 4370-4374.
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TY - JOUR
DO - 10.1021/jo000225s
UR - https://pubs.acs.org/doi/10.1021/jo000225s
TI - New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol
T2 - Journal of Organic Chemistry
AU - Brosse, Nicolas
AU - Pinto, Maria-Fatima
AU - Jamart-Grégoire, Brigitte
PY - 2000
DA - 2000/06/09
PB - American Chemical Society (ACS)
SP - 4370-4374
IS - 14
VL - 65
PMID - 10891140
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2000_Brosse,
author = {Nicolas Brosse and Maria-Fatima Pinto and Brigitte Jamart-Grégoire},
title = {New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol},
journal = {Journal of Organic Chemistry},
year = {2000},
volume = {65},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/jo000225s},
number = {14},
pages = {4370--4374},
doi = {10.1021/jo000225s}
}
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Brosse, Nicolas, et al. “New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol.” Journal of Organic Chemistry, vol. 65, no. 14, Jun. 2000, pp. 4370-4374. https://pubs.acs.org/doi/10.1021/jo000225s.