RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
          
          https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
        Synthesis  2008(15): 2412-2416  
DOI: 10.1055/s-2008-1067187
   DOI: 10.1055/s-2008-1067187
PAPER
© Georg Thieme Verlag
      Stuttgart ˙ New YorkSynthesis of Phosphaisocoumarin Acids via Me3SiX-Mediated Dealkylation Reaction
Weitere Informationen
            
               
                  
                        
                              Received
                              25 March 2008 
                      
Publikationsdatum:
25. Juli 2008 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
25. Juli 2008 (online)
Abstract
The dealkylation of phosphaisocoumarin esters was studied under various conditions. An effective way to synthesize phosphaisocoumarin acids was developed via the reaction of phosphaisocoumarin esters with Me3SiBr in chloroform followed by treatment with methanol, or with Me3SiCl and NaI in acetonitrile followed by hydrolysis, under mild conditions in good to excellent yields.
Key words
synthesis - hydrolysis - dealkylation - phosphorus heterocycle
- 1a 
             
            Handbook of Organophosphorus Chemistry
              
             
            
Engel R. Marcel Dekker; New York: 1992. Chap. 11. - 1b 
             
            A Guide
               to Organophosphorus Chemistry
              
             
            
Quin LD. Wiley; New York: 2000. Chap. 11. - 2a 
             
            
Peng A.-Y.Ding Y.-X. J. Am. Chem. Soc. 2003, 125: 15006 - 2b 
             
            
Peng A.-Y.Ding Y.-X. Org. Lett. 2004, 6: 1119 - 2c 
             
            
Peng A.-Y.Ding Y.-X. Tetrahedron 2005, 61: 10303 - 3 
             
            
Eberhard A.Westheimer FH. J. Am. Chem. Soc. 1965, 87: 253 - 4 
             
            
Mereyala HB.Pathuri G. Synthesis 2006, 2944 - 5a 
             
            
Macomber RS.Krudy GA. J. Org. Chem. 1981, 46: 4038 - 5b 
             
            
Miles JA.Grabiak RC.Cummins C. J. Org. Chem. 1982, 47: 1677 - 5c 
             
            
Mukhametov FS.Korshin EE.Korshunov RL.Efremov YuY.Zyablikova TA. Zh. Obshch. Khim. 1986, 56: 1781 ; Chem. Abstr. 1987, 107, 576105 - 5d 
             
            
Nifant’ev EE.Popkova TN.Kukhareva TS.Bekker AR. Zh. Obshch. Khim. 1988, 58: 1550 ; Chem. Abstr. 1989, 110, 212940 - 6a 
             
            
Fernandez MC.Diaz A.Guillin JJ.Blanco O.Ruiz M.Ojea V. J. Org. Chem. 2006, 71: 6958 - 6b 
             
            
Ruiz M.Fernandez C.Diaz A.Quintela JM.Ojea V. J. Org. Chem. 2003, 68: 7634 - 6c 
             
            
Stoianova DS.Hanson PR. Org. Lett. 2001, 3: 3285 - 7 
             
            
Ghosh S.Tuhina K.Bhowmik DR.Venkateswaran RV. Tetrahedron 2006, 63: 644 - 8 
             
            
Peng A.-Y.Ding Y.-X. Heteroat. Chem. 2005, 16: 529 - 9 
             
            
Kenner W. J. Chem. Soc. 1955, 522