American Chemical Society (ACS)
Organic Letters
,  volume 24 ,  issue 26 ,  pages 4762-4765

Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions

Publication type: Journal Article
Publication date: 2022-06-24
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An attempted Regitz diazo transfer onto homophthalic anhydride led to the discovery of an unexpected ring contraction, which gave N-sulfonyl phthalide-3-carboxamide derivatives. The reaction is thought to proceed via a [3 + 2] cycloaddition of the substrate's enol form and the azide followed by a two-step fragmentation of the intermediate 1,2,3-triazoline with a loss of the nitrogen molecule.
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Kazantsev A. et al. Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions // Organic Letters. 2022. Vol. 24. No. 26. pp. 4762-4765.
GOST all authors (up to 50) Copy
Kazantsev A., Bakulina O., Dar’in D., Kantin G., Bunev A., Krasavin M. Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions // Organic Letters. 2022. Vol. 24. No. 26. pp. 4762-4765.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.2c01730
UR - https://doi.org/10.1021/acs.orglett.2c01730
TI - Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions
T2 - Organic Letters
AU - Kazantsev, Alexander
AU - Bakulina, Olga
AU - Dar’in, Dmitry
AU - Kantin, Grigory
AU - Bunev, Alexander
AU - Krasavin, Mikhail
PY - 2022
DA - 2022/06/24
PB - American Chemical Society (ACS)
SP - 4762-4765
IS - 26
VL - 24
PMID - 35749721
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Kazantsev,
author = {Alexander Kazantsev and Olga Bakulina and Dmitry Dar’in and Grigory Kantin and Alexander Bunev and Mikhail Krasavin},
title = {Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.2c01730},
number = {26},
pages = {4762--4765},
doi = {10.1021/acs.orglett.2c01730}
}
MLA
Cite this
MLA Copy
Kazantsev, Alexander, et al. “Unexpected Ring Contraction of Homophthalic Anhydrides under Diazo Transfer Conditions.” Organic Letters, vol. 24, no. 26, Jun. 2022, pp. 4762-4765. https://doi.org/10.1021/acs.orglett.2c01730.