Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
          
          https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
        Synthesis  2001(12): 1772-1774
DOI: 10.1055/s-2001-17515
   DOI: 10.1055/s-2001-17515
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New YorkTetrabutylammonium Peroxydisulfate in Organic Synthesis; XI. [1] A Novel and Selective Approach to the Oxidative Deprotection of Allyl Ethers with Tetrabutylammonium Peroxydisulfate
Further Information
            
               
                  
                        
                              Received
                              7 May 2001 
                      
Publication Date:
11 August 2004 (online)
            
         
      
   Publication History
Publication Date:
11 August 2004 (online)

Abstract
A tetrabutylammonium peroxydisulfate-mediated oxidative procedure for the mild selective deprotection of allyl ethers to form the corresponding alcohols is described. The alcohols are obtained in yields of 81-85% and the method is compatible with several functional groups under these reaction conditions.
Key words
tetrabutylammonium peroxydisulfate - allyl ethers - protecting group - deprotection
- 1 For Part X see:  
            Chen FE.Fu H.Meng G.Cheng Y.Lu YX. Synthesis 2000, 1519
- 2a 
             
            Green TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1991. p.42
- 2b 
             
            Schelhaas M.Waldmann H. Angew. Chem. Int. Ed. Engl. 1996, 35: 2056
- 2c 
             
            Ranu BC.Bhar S. Org. Prep. Proc. Int. 1996, 28: 371
- 3a 
             
            Gigg R.Warren CD. J. Chem. Soc., Chem. Commun. 1968, 1903
- 3b 
             
            Cunningham J.Gigg R.Warren CD. Tetrahedron Lett. 1964, 1191
- 3c 
             
            Oltvoort JJ.VanBoeckel CAA.DeKoning JH.VanBoom JH. Synthesis 1981, 305
- 3d 
             
            Baudry D.Ephritikhine M.Felkin H. J. Chem. Soc., Chem. Commun. 1978, 694
- 3e 
             
            Corey EJ.Suggs JW. J. Org. Chem. 1973, 38: 3223
- 3f 
             
            Boons G.-J.Burton A.Isles S. Chem. Commun. 1996, 141
- 4 
             
            Diaz RR.Melagatejo CR.Espinosa MTPL.Cubero II. J. Org. Chem. 1994, 59: 7928
- 5 
             
            Lee J.Cha JK. Tetrahedron Lett. 1996, 37: 3663
- 6 
             
            Yadav JS.Chandrasekhar S.Sumitra G.Kacke R. Tetrahedron Lett. 1996, 37: 6603
- 7 
             
            Espanet B.Bunach E.Perichon Y. Tetrahedron Lett. 1992, 33: 2485
- 8 
             
            Honda M.Morita H.Nagakura I. J. Org. Chem. 1997, 62: 8932
- 9 
             
            Mereyala HB.Guntha S. Tetrahedron Lett. 1993, 34: 6929
- 10 
             
            Yu B.Li B.Zhang J.Hui Y. Tetrahedron Lett. 1998, 39: 4871
- 11 
             
            Ito H.Taguch T.Hanzawa Y. J. Org. Chem. 1993, 58: 774
- 12 
             
            Thomas RM.Mohan GH.Iyenger DS. Tetrahedron Lett. 1996, 38: 4721
- 13 
             
            Kamal A.Laxman E.Rao NV. Tetrahedron Lett. 1999, 40: 371
- 14 
             
            Opatz T.Kunz H. Tetrahedron Lett. 2000, 41: 10185
- 15 
             
            Chen FE.Peng ZZ.Fu H.Meng G.Cheng Y.Lü YX. Synlett 2000, 627
- 16 
             
            Manthorpe PA.Gigg R. Methods Carbohydr. Chem. 1980, 8: 305
- 17 
             
            Jung JC.Chai HC.Kim YH. Tetrahedron Lett. 1993, 34: 3581
- 18 
             
            Fischer E. Ber. Dtsch. Chem. Ges. 1895, 28: 1145
 
    