SRN1 Reaction of 2,2,2-Trifluoroethyl Halides with Carbanion

Chem. J. Chinese Universities ›› 2002, Vol. 23 ›› Issue (11): 2080.

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S_RN1 Reaction of 2,2,2-Trifluoroethyl Halides with Carbanion

XU Yong-Jun¹, YANG Xiao-Xi¹, CHEN Qing-Yun², LIN Yuan-Bin³, YE Guo-Xing¹, DING Jing¹

1. The Key Lab of Enhanced Heat Transfer and Energy Conservation, South China University of Technology, Guangzhou 510640;
2. Shanghai Institute of Organic Chemistry, Shanghai 200032;
3. Chemical College of Xiangtian University, Xiangtan 411105, China

Received:2001-09-13 Online:2002-11-24 Published:2002-11-24

Abstract

Abstract: In organic chemistry, the radical nucleophilic substitution of alkyl halides or S RN1 mechanism is one of the most important parts of single electron-transfer (SET) reaction 2,2,2-trifluoroethyl iodide, bromide, chloride except fluoride reacted with carbanion in DMF under laboratory illumination at a specified temperature for 12 h to give the 2,2,2-trifluoroehtyl derivatives and coupling products of two R₁R₂R₃C-. The acceleration by UV irradiation, suppression by p-dinitrobenzene or hydro-quinone showed that the reactions occurred by S_RN1 mechanism. The initiation step may be spontaneous or thermal electron transfer between carbanion and halides because the reactions could occur in dark.

Key words: 2,2,2-Trifluoroethyl halides, Radical nucleophilic substitution of alkyl halides, Carbanion

CLC Number:

O623.2

TrendMD:

XU Yong-Jun, YANG Xiao-Xi, CHEN Qing-Yun, LIN Yuan-Bin, YE Guo-Xing, DING Jing. S_RN1 Reaction of 2,2,2-Trifluoroethyl Halides with Carbanion[J]. Chem. J. Chinese Universities, 2002, 23(11): 2080.

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S_RN1 Reaction of 2,2,2-Trifluoroethyl Halides with Carbanion

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