ELECTROCHEMICAL REDUCTION OF O-NITROPHENOXY COMPOUNDS - AN ACCESS TO 2H-1,4-BENZOXAZINE DERIVATIVES

Authors
MOUATS C HAZARD R RAOULT E TALLEC A
Citation
C. Mouats et al., ELECTROCHEMICAL REDUCTION OF O-NITROPHENOXY COMPOUNDS - AN ACCESS TO 2H-1,4-BENZOXAZINE DERIVATIVES, Bulletin de la Societe chimique de France, 131(1), 1994, pp. 71-77
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
131
Issue
1
Year of publication
1994
Pages
71 - 77
Database
ISI
SICI code
0037-8968(1994)131:1<71:EROOC->2.0.ZU;2-S
Abstract
The electrochemical behavior of o-nitrophenoxyacetophenone, o-nitrophe noxyacetic acid and some related compounds (methyl ester, amide, nitri le) has been investigated in protic media. Controlled potential reduct ions allow the preparation of 2H-1,4-benzoxazine derivatives from the cyclization of the corresponding phenylhydroxylamines, but the latter can also disproportionate. In some cases, a retrocyclization was obser ved in warm acidic media, followed by a rearrangement of the parent ph enylhydroxylamine.