Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 15
244
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Use of Magnesium (Turnings) as a Powerful Catalyst for the O-Acylative Cleavage of Tetrahydrofuran

&
Pages 2309-2314 | Received 19 Feb 2010, Published online: 25 May 2011

REFERENCES

  • (a) Bhatt , M. V. ; Kulkarni , S. U. Cleavage of ethers . Synthesis 1983 , 249 – 282 ; (b) Maercker , A. Ether cleavage with organo-alkali-metal compounds and alkali metals . Angew Chem., Int. Ed. Engl. 1987 , 26 , 972 – 989 ; (c) Zhang , C. ; Price , L. M. ; Daly , W. H. Synthesis and characterization of a trifunctional aminoamide cellulose derivative . Biomacromolecules 2006 , 7 , 139 – 145 .
  • Cloke , J. B. ; Pilgrim , F. J. The reaction of tetrahydrofuran and 2,5-dimethyltetrahydrofuran with acyl halides . J. Am. Chem. Soc. 1939 , 61 , 2667 – 2669 .
  • Ganem , B. ; Small , Jr. V. R. Ferric chloride in acetic anhydide: Mild and versatile reagent for the cleavage of ethers . J. Org. Chem. 1974 , 39 , 3728 – 3730 .
  • Alper , H. ; Huang , C. C. Group VI metal carbonyl–catalyzed reaction of ethers and acid halides . J. Org. Chem. 1973 , 38 , 64 – 71 .
  • Guo , Q. ; Miyaji , T. ; Gao , G. ; Hara , R. ; Takahashi , T. Catalytic C–O bond cleavage of ethers using group 5 or 6 metal halide/acid chloride systems . J. Chem. Soc., Chem. Commun. 2001 , 1018 – 1019 .
  • Kwon , D. W. ; Kim , Y. H. Highly regioselective cleavages and iodinations of cyclic ethers utilizing SmI2 . J. Org. Chem. 2002 , 67 , 9488 – 9491 .
  • Pri-Bar , I. ; Stille , J. K. Acylative cleavage of ethers catalyzed by triorganotin halides and palladium(II) complexes . J. Org. Chem. 1982 , 47 , 1215 – 1220 .
  • Iqbal , J. ; Srivastava , R. R. A practical synthesis of D-malate esters from L-tartrate esters. Tetrahedron 1991 , 47 , 3155 – 3158 .
  • (a) Oku , A. ; Harada , T. ; Kita , K. Selective cleavage of ethers by sodium iodide–acyl chloride . Tetrahedron Lett. 1982 , 23 , 681 – 684 ; (b) Mimero , P. ; Saluzzo , C.; Amouroux, R. Regiocontrolled ring opening of 2-methyltetrahydrofuran with acid chlorides and iodides . Tetrahedron Lett. 1994 , 35 , 1553 – 1556 .
  • Taniguchi , Y. ; Tanaka , S. ; Kitamura , T. ; Fujivara , Y. Lanthanoid-catalyzed ring-opening reaction of epoxides with acyl halides . Tetrahedron Lett. 1998 , 39 , 4559 – 4560 .
  • Suzuki , Y. ; Matsushima , M. ; Kodomari , M. Graphite-catalyzed acylative cleavage of ethers with acyl halides . Chem. Lett. 1998 , 319 – 320 .
  • Green , L. ; Hemeon , L. ; Singer , R. D. 1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as reaction media for the acylative cleavage of ethers . Tetrahedron Lett. 2000 , 41 , 1343 – 1346 .
  • Yadav , J. S. ; Reddy , B. W. S. ; Reddy , M. K. ; Desh , U. ; Guptha , M. K. Indium(III) bromide–catalyzed cleavage of cyclic and acyclic ethers: An efficient and practical ring opening reaction . J. Mol. Cat., Sec. A 2007 , 271 , 266 – 269 .
  • Suresh , V. ; Suryakiran , N. ; Rajesh , K. ; Selvam , J. J. P. ; Srinivasulu , M. ; Venkateswarlu , Y. Synthesis of chloroesters by the cleavage of cyclic and acyclic ethers using La(NO3)3 · 6H2O as a mild and efficient catalyst under solvent-free conditions . Synth. Commun. 2008 , 38 ( 1 ), 92 – 99 .
  • Ke , W. ; Han , E. H. ; Han , Y. F. ; Kainer , K. ; Luo , A. A. Magnesium—Science, technology, and applications. Materials Science Forum 2005, 488–489, 975.
  • (a) Jensean , F. K. ; Bedard , R. Cleavage of tetrahydrofuran by triphenylmethylmagnesium bromide . J. Org. Chem. 1959 , 24 , 874 – 875 .
  • Pansare , S. V. ; Malusare , M. G. ; Rai , A. N. Magnesium bromide–catalysed acylation of alcohols . Synth. Commun. 2000 , 30 , 2587 – 2592 .
  • Svoboda , J. ; Nic , M. ; Palecek , J. Application of magnesium alkoxides to syntheses of benzoheterocyclic compounds . Coll. of Czechoslovak Chem. Commun. 1993 , 58 , 592 – 599 .
  • (a) Pasha , M. A. ; Myint , Y. Y. Ultrasound-assisted synthesis of δ-chloroesters from tetrahydrofuran and acyl chlorides in the presence of catalytic zinc dust . Ultrason. Sonochem. 2005 , 13 , 175 – 179 ; (b) Pasha , M. A. ; Manjula , K. Simple and efficient method for the synthesis of δ-chloroesters from tetrahydrofuran and acyl chlorides in the presence of catalytic iodine . Synth. Commun. 2007 , 37 , 927 – 932 .
  • Vogel , A. I. A Textbook of Practical Organic Chemistry, , 3rd ed ; ELBS : London , 1975 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.