ELECTROCHEMICAL ADDITION OF CHLORODIFLUOROACETYL AROMATIC-COMPOUNDS TO ELECTRON-RICH OLEFINIC SUBSTRATES - A CONVENIENT SYNTHESIS OF GEM-DIFLUORO HETEROCYCLIC-COMPOUNDS

被引：18

作者：

MEDEBIELLE, M

机构：

[1] Laboratoire d'Electrochimie Moléculaire, l'Université Denis Diderot (Paris 7), Associée au CNRS, 75251 Paris Cedex 05

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 12期

关键词：

D O I：

10.1016/0040-4039(95)00222-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Indirect electrochemical reduction in acetonitrile of N,N-dimethyl-4-(chlorodifluoroacetyl)-1-napthylamine and of N,N-dimethyl-2,4-bis(chlorodifluoroacetyl)-1-napthylamine in the presence of electron-rich olefinic substrates yields gem-difluoro heterocyclic compounds after intramolecular cyclization of a gamma,gamma,-difluoroalkyl radical.

引用

页码：2071 / 2074

页数：4

共 24 条

[1] OUTER-SPHERE DISSOCIATIVE ELECTRON-TRANSFER TO ORGANIC-MOLECULES - A SOURCE OF RADICALS OR CARBANIONS - DIRECT AND INDIRECT ELECTROCHEMISTRY OF PERFLUOROALKYL BROMIDES AND IODIDES
ANDRIEUX, CP
GELIS, L
MEDEBIELLE, M
PINSON, J
SAVEANT, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) : 3509 - 3520
[2] UNUSUAL REACTIONS RESULTING FROM THE ADDITION ON OLEFINS OF TRIFLUOROMETHYL RADICALS OBTAINED FROM DISSOCIATIVE ELECTRON-TRANSFER BETWEEN ELECTROCHEMICALLY GENERATED AROMATIC ANION RADICALS AND TRIFLUOROMETHYL BROMIDE
ANDRIEUX, CP
GELIS, L
SAVEANT, JM
[J]. TETRAHEDRON LETTERS, 1989, 30 (37) : 4961 - 4964
[3] ARNONE A, 1992, TETRAHEDRON, V48, P8523
[4] Banks R. E., 1979, ORGANOFLUORINE CHEM
[5] BARTH F, 1991, TETRAHEDRON LETT, V42, P5873
[6] AN EFFICIENT ELECTROCHEMICAL ROUTE TO (PERFLUOROALKYL)ALKYNES
CALAS, P
MOREAU, P
COMMEYRAS, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (08) : 433 - 434
[7] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1.
CURRAN, DP
[J]. SYNTHESIS-STUTTGART, 1988, (06): : 417 - 439
[8] 2,2-DIFLUORO-3-HYDROXYESTERS BY REFORMATSKII REACTION
HALLINAN, EA
FRIED, J
[J]. TETRAHEDRON LETTERS, 1984, 25 (22) : 2301 - 2302
[9] SYNTHESIS OF 2-DEOXY-2,2-DIFLUORO-D-RIBOSE AND 2-DEOXY-2,2-DIFLUORO-D-RIBOFURANOSYL NUCLEOSIDES
HERTEL, LW
KROIN, JS
MISNER, JW
TUSTIN, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) : 2406 - 2409
[10] NUCLEOPHILIC NITROGEN-NITROGEN EXCHANGE-REACTION AT AROMATIC CARBON-ATOMS - REACTION OF N,N-DIMETHYL-2,4-BISTRIFLUOROACETYL-1-NAPHTHYLAMINE WITH VARIOUS AMINES
HOJO, M
MASUDA, R
OKADA, E
[J]. TETRAHEDRON LETTERS, 1987, 28 (49) : 6199 - 6200

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