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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 8
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Original Articles

Reductive Cleavage of 2,2,2-Trichloroethyl Esters with Sodium Telluride

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Pages 1405-1414 | Received 16 Sep 1997, Published online: 22 Aug 2006

REFERENCES

  • Kocienski , P. J. 1994 . Protecting Groups , Stuttgart : Georg Thieme Verlag .
  • Greene , T. W. and Wuts , P. G.M. 1991 . Protective groups in Organic Synthesis , New York : John Wiley & sons inc. .
  • Woodward , R. B. , Hensler , K. , Gosteli , J. , Naegeli , R. , Oppolzer , W. , Ramage , R. , Ranganathan , S. and Korbrüggen , H. 1966 . J. Am. Chem. Soc. , 88 : 852
  • Semmelhack , M. F. and Heinshon , G. E. 1972 . J. Am. Chem. Soc. , 94 : 5139
  • Huang , Z-Z. and Zhou , X-J. 1989 . Synthesis , : 693
  • Blay , G. , Cardona , L. , García , B. and Pedro , J. R. 1995 . Synlett , : 1189
  • Blay , G. , Cardona , L. , García , B. , Lahoz , L. and Pedro , J. R. 1996 . Tetrahedron , 52 : 8611
  • Bargues , V. , Blay , G. , Fernández , I. and Pedro , J. R. 1996 . Synlett , : 655
  • Chen , J. and Zhou , X-J. 1987 . Synthetic Comm. , 17 : 161
  • Huang , Z-Z. and Zhou , X-J. 1990 . Synthesis , : 633
  • Sodium hydrogen telluride catalyzed transesterifications of alkyl and aryl esters of aromatic carboxylic acids to ethyl esters in EtOH have been reported previously. In order to test the role of sodium telluride in the transesterifcation of 1d the following blank probe was carried out: Sodium borohydride (1.5 eq) was refluxed in ethanol for 45 minutes, and to the resulting solution was added 1d at room temperature. After completion of the starting material, a ca. 9:1 (GC-MS) mixture of ethyl undecylenate and 11-undecenol resulting from the reduction of the ester group was obtained. It seems from this reult that NaTeH is not essential in this case. See: Suresh J. R. Mohan P. S. Shanmugam P. Indian J. Chem. Sect. B 1994 33B 290
  • Barton , D. H.R. and McCombie , S. W. 1975 . J. Chem. Soc. Perkin Trans. I , : 1574
  • Hamada , Y. , Kondo , Y. , Shibata , M. and Shioiri , T. J. 1989 . J. Am. Chem. Soc. , 111 : 669
  • Bargues , V. , Blay , G. , Cardona , L. , García , B. and Pedro , J. R. 1995 . Tetrahedron Lett. , 36 : 8469
  • Francisco , C. G. , Freire , R. , Rodríguez , M. S. and Suárez , E. 1991 . Tetrahedron Lett. , 32 : 3413

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