Chinese Journal of Magnetic Resonance

Previous Articles     Next Articles

The NMR Study on the Intramolecular Cyclization of a, a-Bis(2-Hydroxyethyl)phenylacetonitrile

GAO Zhen-hua,HE Xiao-wei,GUO Yong-biao,ZOU Chuan-pin*    

  1. Beijing Pharmaceutical Chemistry Institute, Beijing 102205, China

     
  • Received:2014-02-21 Revised:2014-03-05 Online:2014-06-05 Published:2014-06-05
  • About author:*Corresponding author:ZOU Chuan-pin, Tel: 010-66758947, E-mail: zou404@gmail.com.

Abstract:

a, a-Bis(2-hydroxyethyl)phenylacetonitrile (2a) was efficiently synthesized from phenylacetonitrile, lithium diisopropylamide and ethylene oxide by one-pot method. Through the analysis with 1H NMR, 13C NMR, DEPT, HSQC, HMBC spectra, it has proved that there is a tautomerism caused by intramolecular cyclization. This phenomena can be used to explain the low yield of piperidine derivatives synthesized from compounds 2avia mesylation and cyclization.

Key words: NMR, structure analysis, 2D NMR, a, a-bis(2-hydroxyethyl), tautomerism

CLC Number: