Synlett 2012(2): 319-320  
DOI: 10.1055/s-0031-1290126
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Phosphoric Trichloride

Haibao Duan*
School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P. R. of China
e-Mail: duan4588@163.com;
Further Information

Publication History

Publication Date:
04 January 2012 (online)

Introduction

Phosphoric trichloride is a colorless, clear and transparent irritating liquid. Its structure is a tetrahedral consisting of one P=O double bond and three P-Cl bonds. POCl3 reacts with alcohols to produce alkyl phosphate esters and is therefore a versatile phosphating agent. [¹] As a selective and inexpensive reagent giving high yields in simple operations under mild conditions, it is tremendously used in organic synthesis, for example, in chlorination, [²] regiospecific dehydration and ring-closing reactions. [³] Its use has been reported in several types of name reactions, for example, in the Bischler-Napieralski [4] and Vilsmeier-Haack reactions. [5]

Figure 1 Phosphoric trichloride

    References

  • 1 Muramatsu N. Takenish T. J. Org. Chem.  1965,  30:  3211 
  • 2 Robiins RK. Christensen BE. J. Am. Chem. Soc.  1952,  74:  3624 
  • 3 Meth-Cohn O. Rhouati S. Tarnowski B. Bobinson A.
    J. Chem. Soc., Perkin Trans. 1  1981,  1537 
  • 4 Fodor G. Gal J. Phillips BA. Angew. Chem. Int. Ed.  1972,  11:  919 
  • 5 Alunni S. Linda P. Marino G. Santini S. Savelli G. J. Chem. Soc., Perkin Trans. 2  1972,  2070 
  • 6 Gurjar MK. Pramanik V. Bhattasali D. Ramana CV. Mohapatra DK. J. Org. Chem.  2007,  72:  6591 
  • 7 Shing TKM. Cheng HM. Wong WF. Kwong CSK. Li JM. Lau CBS. Leung PS. Cheng CHK. Org. Lett.  2008,  10:  3146 
  • 8 Liu J. Wang M. Han F. Liu YY. Liu Q. J. Org. Chem.  2009,  74:  5090 
  • 9 Lang S. Groth U. Angew. Chem. Int. Ed.  2009,  48:  911 
  • 10 Pérez M. Contelles JM. Synthesis  2009,  3649