Aromatic trifluoromethyldenitration and trifluoromethyldecyanation using trifluoromethyltrimethylsilane

被引：12

作者：

Adams, DJ ^{[1
]}

Clark, JH ^{[1
]}

Hansen, LB ^{[1
]}

Sanders, VC ^{[1
]}

Tavener, SJ ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO1 5DD, N Yorkshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 18期

关键词：

D O I：

10.1039/a805079a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Activation of trifluoromethyltrimethylsilane by potassium fluoride in N,N-dimethylacetamide provides a powerful source of trifluoromethide which is capable of substituting aromatic nitro and cyano groups under nucleophilic conditions, albeit in low yield. The trifluoromethide generated in this system is also a potent base which leads to a number of interesting side reactions via deprotonation of the substrate.

引用

页码：3081 / 3085

页数：5

共 23 条

[11] FRY JL, 1983, J ORG CHEM, V12, P2112
[12] FURNISS BS, 1989, VOGELS TXB PRACTICAL, P855
[13] KATRITZKY AR, 1989, SYNTHESIS-STUTTGART, P949
[14] REACTIONS OF FLUORIDE AND NITRITE IONS WITH 4-NITROPHTHALIMIDES
MARKEZICH, RL
ZAMEK, OS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (21) : 3431 - 3434
[15] PHOTOCHEMICAL-REACTION OF ARENECARBONITRILES IN THE PRESENCE OF ALKYLSILANES, SILYL ETHERS AND SILYL AMINES
MELLA, M
DALESSANDRO, N
FRECCERO, M
ALBINI, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (03): : 515 - 519
[16] THE MONO-ALKYLDECYANATION OF TETRAFLUOROTEREPHTHALONITRILE BY REACTION WITH GRIGNARD-REAGENTS
MILNER, DJ
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 302 (02) : 147 - 152
[17] Patai S., 1989, The Chemistry of Organic Silicon Compounds
[18] Perfluoroalkylation with organosilicon reagents
Prakash, GKS
Yudin, AK
[J]. CHEMICAL REVIEWS, 1997, 97 (03) : 757 - 786
[19] PRAKASH GKS, 1992, SYNTHETIC FLUORINE C, pCH10
[20] Reichardt C. R. C., 1988, SOLVENTS SOLVENT EFF

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