Anionotropic Rearrangements of 3-Bromo-1-(2-nitrophenyl)­propan-1-ols and Their Esters in Fluorosulfonic Acid

Kinetically controlled reaction of 3-bromo-1-(2-nitrophenyl)propan-1-ols and their formic acid esters with fluorosulfonic acid afforded 3-(2-bromoethyl)-1-oxo-1,3-dihydro-2,1-benzoxazol-1-ium and 6-bromo-3-(2-bromoethyl)-1-oxo-1,3-dihydro-2,1-benzoxazol-1-ium fluorosulfonates. As the reaction mixtur...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2021-10, Vol.57 (10), p.1656-1661
Main Authors: Bandaev, S. G., Gulov, T. Y., Murodov, D. S.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Esters
Formic acid
Organic Chemistry
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Summary:Kinetically controlled reaction of 3-bromo-1-(2-nitrophenyl)propan-1-ols and their formic acid esters with fluorosulfonic acid afforded 3-(2-bromoethyl)-1-oxo-1,3-dihydro-2,1-benzoxazol-1-ium and 6-bromo-3-(2-bromoethyl)-1-oxo-1,3-dihydro-2,1-benzoxazol-1-ium fluorosulfonates. As the reaction mixture was kept at 20°C, these ions underwent anionotropic rearrangements leading to the formation of 3-bromomethyl-1-oxo-3,4-dihydro-1 H -2,1-benzoxazin-1-ium, 4-bromo-3-methyl-1-oxo-3,4-dihydro-1 H -2,1-benzoxazin-1-ium, and 5-bromo-1-oxo-1,3,4,5-tetrahydro-2,1-benzoxazepin-1-ium fluorosulfonates. The complete transformation was achieved in 84 h after dissolution of the initial 3-bromo-1-(2-nitrophenyl)propan-1-ols or their esters.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428021100146