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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 3
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Original Articles

Optimization of the Microwave-Assisted Ortho Ester Claisen Rearrangement: Application to Monoterpenols

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Pages 462-468 | Received 02 Feb 2009, Published online: 06 Jan 2010

REFERENCES

  • Johnson , W. S. ; Werthemann , L. ; Bartlett , W. R. ; Brocksom , T. J. ; Li , T. T. ; Faulkner , D. J. ; Petersen , M. R. A simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds: Synthesis of squalene . J. Am. Chem. Soc. 1970 , 92 , 741 – 743 .
  • (a) Claisen , L. Rearrangement of phenyl allyl ethers in C-allylphenols . Chem. Ber. 1912 , 45 , 3157 – 3166 ; (b) Ziegler , F. E. The thermal, aliphatic Claisen rearrangement . Chem. Rev. 1988 , 88 , 1423 – 1452 .
  • Loupy , A. Microwaves in Organic Synthesis, , 2nd ed. ; Wiley-VCH : Weinheim , 2006 .
  • Chemat-Djenni , Z. ; Hamada , B. ; Chemat , F. Atmospheric pressure microwave assisted heterogeneous catalytic reactions . Molecules 2007 , 12 , 1399 – 1409 .
  • Hedidi , M. ; Hamdi , S. M. ; Mazari , T. ; Boutemeur , B. ; Rabia , C. ; Chemat , F. ; Hamdi , M. Microwave-assisted synthesis of calix[4]resorcinarenes . Tetrahedron 2006 , 62 , 5652 – 5655 .
  • Roberts , B. A. ; Strauss , C. R. Toward rapid, “green,” predictable microwave-assisted synthesis . Acc. Chem. Res. 2005 , 38 , 653 – 661 .
  • De la Hoz , A. ; Diaz-Ortiz , A. ; Moreno , A. Microwaves in organic synthesis: Thermal and non-thermal microwave effects . Chem. Soc. Rev. 2005 , 34 , 164 – 178 .
  • Srikrishna , A. ; Nagaraju , S. ; Kondaiah , P. Application of microwave heating technique for rapid synthesis of γ,δ-unsaturated esters . Tetrahedron 1995 , 51 , 1809 – 1816 .
  • Abramovitch , R. A. Applications of microwave energy in organic chemistry: A review. Org. Prep. Proc. Int. 1991, 23, 683–711.
  • Tymoshenko , D. O. Microwave-assisted Claisen and aza-Claisen rearrangements . Mini-Rev. Org. Chem. 2008 , 5 , 85 – 95 .
  • Herrero , M. A. ; Kremsner , J. M. ; Kappe , C. O. Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry . J. Org. Chem. 2008 , 73 , 36 – 47 .
  • Paruch , E. ; Ciunik , Z. ; Nawrot , J. ; Wawrzenczyk , C. Lactones, 9: Synthesis of terpenoid lactones active insect antifeedants . J. Agric. Food Chem. 2000 , 48 , 4973 – 4977 .
  • Günther , H. J. ; Guntrum , E. ; Jäger , V. Synthese von 4-Penten-4-oliden(γ-Methylen-α-butyrolactonen) über 4-Pentensäuren . Lieb. Ann. Chem. 1984 , 15 – 30 .

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