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Citation: QI Xin, XU Li, PENG Xiao-Jun. 1,2 Elimination of syn Diethyl (2-acetylamino-1-bromo-2-(p-methoxyphenyl)ethyl) phosphonate under Basic Condition[J]. Chinese Journal of Applied Chemistry, ;2005, 22(2): 180-183. shu

1,2 Elimination of syn Diethyl (2-acetylamino-1-bromo-2-(p-methoxyphenyl)ethyl) phosphonate under Basic Condition

QI Xin ^a ,
XU Li ^b,, ,
PENG Xiao-Jun ^a

1.
a School of Chemical Engineering, Dalian University of Technology, Dalian;
2.
b Information College of Science and Technology, Nanjing Forestry University, Nanjing 210037

Corresponding author: XU Li,
Received Date: 19 March 2004
Available Online: 6 July 2004
Fund Project: 南京林业大学创新基金资助项目(CX030701) (CX030701)

A preferential 1,2 elimination reaction of syn diethyl (2-acetylamino-1-bromo-2-(p-methoxy-phenyl)ethyl)phosphonate 1 rather than the anticipated nucleophilic substitution reaction under basic conditions is described in the present paper. The product was characterized by IR, HRMS and NMR spectra. The relatively low ability of the α bromine as a leaving group compared to that of the mesylate group reported in the literature should be attributed to the low degree of conversion when K₂CO₃ was used. And when 1,8-diazabicyclo-undec-7-ene(DBU) was used, the more sensitivity towards the base of the β proton caused by the induction effect from the higher electronegative α bromine atom should account for the elimination reaction. Without the base, the failure of the displacement of the bromine atom by benzotriazole should be due to the poor leaving ability of bromine as well as the steric hindrance from the bulky phosphonate group.
- elimination,
- aminobromination,
- phosphonate,
- 2D NMR
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