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 2004(4): 568-572
DOI: 10.1055/s-2004-815944
DOI: 10.1055/s-2004-815944
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Simple and Facile Carboxylation Method and Its Application for Synthesis of Liquid Crystals
Further Information
Received
25 November 2003
Publication Date:
03 February 2004 (online)
Publication History
Publication Date:
03 February 2004 (online)
Abstract
Sonication of a mixture of magnesium powder, 1,2-dibromoethane, aryl bromide and diethyl dicarbonate in THF followed by treatment with BF3·OEt2 at room temperature afforded aryl ester with reasonable yield. A series of aryl bromides were investigated and transformed to their corresponding aryl esters under the reaction conditions.
Key words
carboxylation - Barbier reaction - diethyl dicarbonate - Lewis acid - liquid crystal
- 1
Larock RC. Comprehensive Organic Transformations: A Guide to Functional Group Preparations 2nd ed.: John Wiley & Sons Inc.; New York: 1999. - 2
Olah GA.Torok B.Joschek JP.Bucsi I.Esteves PM. J. Am. Chem. Soc. 2002, 124: 11379 - 3
Keramane E.-M.Boyer B.Rogue J.-P. Tetrahedron Lett. 2001, 42: 855 - 4
Smith AB.Leahy JW.Noda I.Remiszewski SW.Liverton NJ.Zibuck R. J. Am. Chem. Soc. 1992, 114: 2995 - 5
Schlosser M.Geneste H. Tetrahedron 1998, 54: 10119 - 6
Satyanarayana G.Sivaram S. Synth. Commun. 1990, 20: 3273 - 7
Marchand A.Maxwell A.Mootoo B.Pelter A.Reid A. Tetrahedron 2000, 56: 7331 - 8
Woodward RB.Hoye TR. J. Am. Chem. Soc. 1977, 99: 8007 - 9
Jung ME.Hagenah JA. J. Org. Chem. 1987, 52: 1889 - 10
Cacchi S.Lupi A. Tetrahedron Lett. 1992, 33: 3939 - 11
Fletcher SR.Burkamp F.Blurton P.Cheng SKF.Clarkson R.O’Connor D.Spinks D.Tudge M.van Niel MB.Patel S.Chapman K.Marwood R.Shepheard S.Bentley G.Cook GP.Bristow LJ.Castro JL.Hutson PH.MacLeod AM. J. Med. Chem. 2002, 45: 492 - 12
Lee AS.-Y.Dai W.-C. Tetrahedron 1997, 53: 859 - 13
Lee AS.-Y.Kung C.-C. J. Chin. Chem. Soc. 1997, 44: 65 - 14
Frey J.Bond AD.Holmes AB. Chem. Commun. 2002, 2424 - 15
Kumar S.Varshney SK. Angew. Chem. Int. Ed. 2000, 39: 3140 - 16
Cayuela R.Nguyen HT.Destrade C.Levelut AM. Mol. Cryst. Liq. Cryst. 1989, 177: 81 - 17
Lupton JM.Samuel IDW.Frampton MJ.Beavington R.Burn PL. Adv. Funct. Mater. 2001, 11: 287 - 18
Wu I.-Y.Lin JT.Tao Y.-T.Balasubramaniam E. Adv. Mater. 2000, 12: 668 - 19
Pelter A.Jenkins I.Jones DE. Tetrahedron 1997, 53: 10357 - 20
Dawson MI.Jong L.Hobbs PD.Cameron JF.Chao W.-r.Pfahl M.Lee M.-O.Shroot B.Pfahl M. J. Med. Chem. 1995, 38: 3368 - 21
Ansell MF. The Chemistry of Acyl HalidesPatai S. Interscience; London: 1972. p.35-68 - 22
Nagano R.Nishikido J.Inazu T.Yoshino T. Bull. Chem. Soc. Jpn. 1973, 46: 653 - 23
Chowdhury C.Kundu NG. Tetrahedron 1999, 55: 7011