Stereoselective Synthesis of Highly Functionalized Trifluoromethylated Cyclobutenes

Mohammad H. Mosslemin; Issa Yavari; Mohammad Anary-Abbasinejad; Mohammad R. Nateghi

doi:10.1055/s-2004-822316

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Stereoselective Synthesis of Highly Functionalized Trifluoromethylated Cyclobutenes

Mohammad H. Mosslemin^a, Issa Yavari*^b, Mohammad Anary-Abbasinejad^a, Mohammad R. Nateghi^a
^a Department of Chemistry, Islamic Azad University, Yazd, Iran
^b Department of Chemistry, University of Tarbiat Modarres, PO Box 14115-175, Tehran, Iran
Fax: +98(21)8006544; e-Mail: isayavar@yahoo.com;

Abstract

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Abstract

1,1,1-Trifluoro-4-arylbutan-2,4-diones undergo a smooth reaction with dialkyl acetylenedicarboxylates and triphenylphosphine to produce phosphorus ylide intermediates, which undergo stereoselective intramolecular Wittig reaction to produce dialkyl 4-arylcarbonyl-3-trifluoromethyl-cyclobut-2-ene-1,2-dicarboxylates in good yields.

Key words

intramolecular Wittig reaction - trifluoromethylated cyclobutenes - ylide chemistry

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References

<A NAME="RP00904SS-1">1</A> Becker KB. Tetrahedron 1980, 36: 1717

<A NAME="RP00904SS-2">2</A> Vollhardt KPC. Synthesis 1975, 765

<A NAME="RP00904SS-3">3</A> Patai S. The Chemistry of Alkenes Wiley; New York: 1964.

<A NAME="RP00904SS-4">4</A> Durst T. Breau L. In Comprehensive Organic Synthesis Selectivity Strategy and Efficiency in Modern Organic Chemistry Vol. 5: Paquette L. Pergamon; New York: 1991. p.675-697

<A NAME="RP00904SS-5">5</A> Moore HW. Decker OHW. Chem. Rev. 1986, 86: 821

<A NAME="RP00904SS-6">6</A> Pollart DJ. Moore HW. J. Org. Chem. 1989, 54: 5444

<A NAME="RP00904SS-7">7</A> Yavari I. Samzadeh-Kermani AR. Tetrahedron Lett. 1998, 39: 6343

<A NAME="RP00904SS-8">8</A> Yavari I. Asghari S. Tetrahedron 1999, 55: 11853

<A NAME="RP00904SS-9">9</A> Yavari I. Nourmohammadian F. J. Chem. Res., Synop. 1999, 512

<A NAME="RP00904SS-10">10</A> Gunther H. NMR Spectroscopy 2nd ed.: Wiley; New York: 1995. Chap. 4.

<A NAME="RP00904SS-11">11</A> Corbridge DEC. Phosphorus An Outline of its Chemistry Biochemistry and Technology Elsevier; Amsterdam: 1995. p.42-47

<A NAME="RP00904SS-12A">12a</A> Kolodiazhynyi OI. Russ. Chem. Rev. 1997, 66: 225

<A NAME="RP00904SS-12B">12b</A> Pietruslcwicz KM. Zablocka M. Chem. Rev., 1983, 109: 83