An Efficient One-Pot Synthesis
of Oxime Ethers from Alcohols Using Triphenylphosphine/Carbon
Tetrachloride

Mohammad Navid Soltani Rad; Ali Khalafi-Nezhad; Fatemeh Karimitabar; Somayeh Behrouz

doi:10.1055/s-0029-1218711

PAPER

An Efficient One-Pot Synthesis of Oxime Ethers from Alcohols Using Triphenylphosphine/Carbon Tetrachloride

Mohammad Navid Soltani Rad*^a, Ali Khalafi-Nezhad*^b, Fatemeh Karimitabar^b, Somayeh Behrouz^a
^a Department of Chemistry, Faculty of Basic Sciences, Shiraz University of Technology, Shiraz 71555-313, Iran
Fax: +98(711)7354523; e-Mail: soltani@sutech.ac.ir; e-Mail: nsoltanirad@gmail.com;
^b Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran

Abstract

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Abstract

A convenient and efficient one-pot O-alkylation of oximes from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, oxime, and DBU in the presence of catalytic amounts of tetrabutylammonium iodide in refluxing acetonitrile regioselectively furnishes the corresponding O-alkyl ethers in good yields. This methodology is highly efficient O-alkylation of oximes with various structurally diverse alcohols. Semiempirical quantum-mechanic calculations (AM1) for unsymmetrical oxime ethers, indicated a lower heat of formation for Z-isomers.

Key words

oxime - alcohol - O-alkylation - triphenylphosphine - carbon tetrachloride - DBU

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References

<A NAME="RZ02510SS-1A">1a</A> March J. Advanced Organic Chemistry 4th ed.: John Wiley & Sons (Asia); Singapore: 2005.

<A NAME="RZ02510SS-1B">1b</A> Kleeman A. Engel J. Kutscher B. Reichert D. Pharmaceutical Substances 3rd ed.: Thieme; Stuttgart: 1999.

<A NAME="RZ02510SS-1C">1c</A> Kassa J. Clin. Toxicol. 2002, 40: 803

<A NAME="RZ02510SS-1D">1d</A> Freeman JP. Chem. Rev. 1973, 73: 283

<A NAME="RZ02510SS-1E">1e</A> Gowenlock BG. Richter-Addo GB. Chem. Rev. 2004, 104: 3315

<A NAME="RZ02510SS-2A">2a</A> Miyabe H. Ushiro C. Naito T. Chem. Commun. 1997, 1789

<A NAME="RZ02510SS-2B">2b</A> Miyabe H. Fujii K. Naito T. Org. Biomol. Chem. 2003, 1: 381

<A NAME="RZ02510SS-2C">2c</A> Miyabe H. Ueda M. Yoshiko N. Yamakawa K. Naito T. Tetrahedron 2000, 56: 2413

<A NAME="RZ02510SS-2D">2d</A> Marco JA. Carda M. Murga J. Conzález F. Falomir E. Tetrahedron Lett. 1997, 38: 1841

<A NAME="RZ02510SS-3A">3a</A> Phillpotts RJ. Delong DC. Wallace J. Jones RW. Reed SE. Tyrrell DAJ. Lancet 1981, 1: 1342

<A NAME="RZ02510SS-3B">3b</A> Hayden FG. Gawaltney JM. Antimicrob. Agents Chemother. 1982, 21: 892

<A NAME="RZ02510SS-3C">3c</A> Miller FD. Monto AS. Delong DC. Exelby A. Bryan ER. Srivastava S. Antimicrob. Agents Chemother. 1985, 27: 102

<A NAME="RZ02510SS-4">4</A> Sakene K. Kawabata K. Inamoto Y. Yamanaka H. Takaya T. Yakugaku Zasshi 1993, 113: 605

<A NAME="RZ02510SS-5A">5a</A> Mixich G. Thiele K. Arzneim.-Forsch. 1979, 29: 1510

<A NAME="RZ02510SS-5B">5b</A> Artico M. Rango R. Porretta GC. Massa S. Musin C. Spiga MG. Carrias S. La Colla P. Med. Chem. Res. 1996, 137

<A NAME="RZ02510SS-5C">5c</A> Wahbi Y. Caujolle R. Tournaire C. Payard M. Linas MD. Seguela JP. Eur. J. Med. Chem. 1995, 30: 955

<A NAME="RZ02510SS-6A">6a</A> Mordi MN. Petta MD. Boote V. Morris GA. Barber J. J. Med. Chem. 2000, 43: 467

<A NAME="RZ02510SS-6B">6b</A> Gharbi-Benarous J. Delaforge M. Jankowski CK. Girault JP. J. Med. Chem. 1991, 34: 1117

<A NAME="RZ02510SS-7A">7a</A> De Clerk F. Beetens J. Van de Water A. Vercammen E. Janssen PAJ. Thromb. Haemostasis 1989, 61: 43

<A NAME="RZ02510SS-7B">7b</A> Bossche HV. Willemsens G. Bellens D. Janssen PAJ. Biochem. Pharmacol. 1992, 43: 739

<A NAME="RZ02510SS-8A">8a</A> Abele E. Abele R. Rubina K. Popelis J. Sleiksa I. Lukevics E. Synth. Commun. 1998, 28: 2621

<A NAME="RZ02510SS-8B">8b</A> Yamada T. Goto K. Mitsuda Y. Tsuji J. Tetrahedron Lett. 1987, 28: 4557

<A NAME="RZ02510SS-8C">8c</A> Karakurt A. Dalkara S. Özalp M. Özbey S. Kendi E. Stables JP. Eur. J. Med. Chem. 2001, 36: 421

<A NAME="RZ02510SS-8D">8d</A> Merkaš S. Litvić M. Cepanec I. Vinković V. Molecules 2005, 10: 1429

<A NAME="RZ02510SS-8E">8e</A> Abele E. Lukevics E. Org. Prep. Proced. Int. 2000, 32: 235

<A NAME="RZ02510SS-8F">8f</A> Banerjee T. Dureja P. Molecules 2005, 10: 990

<A NAME="RZ02510SS-8G">8g</A> Li CB. Cui Y. Zhang WQ. Li JL. Zhang SM. Choi MCK. Chan ASC. Chin. Chem. Lett. 2002, 113: 95

<A NAME="RZ02510SS-8H">8h</A> Li CB. Zhang H. Cui Y. Zhang S. Zhao Z. Choi MCK. Chan ASC. Synth. Commun. 2003, 33: 543

<A NAME="RZ02510SS-9A">9a</A> Nanoppa PD. Pandurangan K. Maitra U. Wailes S. Org. Lett. 2007, 9: 2767

<A NAME="RZ02510SS-9B">9b</A> Mooradian A. Dupont PE.
J. Heterocycl. Chem. 1967, 4: 441

<A NAME="RZ02510SS-10A">10a</A> Jacob BB. Synthesis 1975, 782

<A NAME="RZ02510SS-10B">10b</A> Nesynov EP. Pel’kis PS. Zh. Org. Khim. 1976, 12: 1955

<A NAME="RZ02510SS-11A">11a</A> Soltani Rad MN. Behrouz S. Dianat M. Synthesis 2008, 2055

<A NAME="RZ02510SS-11B">11b</A> Buchalska E. Plenkiewicz J. J. Mol. Catal. B: Enzym. 2001, 11: 255

<A NAME="RZ02510SS-11C">11c</A> Bakunova SM. Grigor’ev IA. Volodarsky LB. Russ. Chem. Bull. 1999, 48: 1389

<A NAME="RZ02510SS-11D">11d</A> Şen N. Kar Y. Kurbanov S. Russ. J. Org. Chem. (Engl. Transl.) 2007, 43: 449

<A NAME="RZ02510SS-11E">11e</A> Donald JR. Edwards MG. Taylor RJK. Tetrahedron Lett. 2007, 48: 5201

<A NAME="RZ02510SS-11F">11f</A> Wan X. Doridot G. Joullié MM. Org. Lett. 2007, 9: 977

<A NAME="RZ02510SS-11G">11g</A> Kliegel W. Justus Liebigs Ann. Chem. 1970, 733: 192

<A NAME="RZ02510SS-12">12</A> Stefani AP. Lacher JR. Park JD. J. Org. Chem. 1960, 25: 676

<A NAME="RZ02510SS-13">13</A> Kolenc I. Kočevar M. Polanc S. Acta Chim. Slov. 1999, 46: 281

<A NAME="RZ02510SS-14A">14a</A> Miyabe H. Yoshida K. Reddy VK. Matsumura A. Takemoto Y. J. Org. Chem. 2005, 70: 5630

<A NAME="RZ02510SS-14B">14b</A> Miyabe H. Matsumura A. Yoshida K. Yamauchi M. Takemoto Y. Synlett 2004, 2123

<A NAME="RZ02510SS-14C">14c</A> Miyabe H. Matsumura A. Moriyama K. Takemoto Y. Org. Lett. 2004, 6: 4631

<A NAME="RZ02510SS-15A">15a</A> Bhuniya D. Mohan S. Narayanan S. Synthesis 2003, 1018

<A NAME="RZ02510SS-15B">15b</A> Bertelsen S. Dinér P. Johansen RL. Jørgensen KA. J. Am. Chem. Soc. 2007, 129: 1536

<A NAME="RZ02510SS-15C">15c</A> Vanderwal CD. Jacobsen EN. J. Am. Chem. Soc. 2004, 126: 14724

<A NAME="RZ02510SS-15D">15d</A> Fouchet B. Joucla M. Messager JC. Toupet L. J. Chem. Soc., Chem. Commun. 1982, 858

<A NAME="RZ02510SS-15E">15e</A> Bhuniya D. Gujjary S. Sengupta S. Synth. Commun. 2006, 36: 151

<A NAME="RZ02510SS-16A">16a</A> Goda H. Sato M. Ihara H. Hirayama C. Synthesis 1992, 849

<A NAME="RZ02510SS-16B">16b</A> Watson KG. Brown RN. Cameron R. Chalmers DK. Hamilton S. Jin B. Krippner GY. Luttick A. McConnell DB. Reece PA. Ryan J. Stanislawski PC. Tucker SP. Wu W.-Y. Barnard DL. Sidwell RW. J. Med. Chem. 2003, 46: 3181

<A NAME="RZ02510SS-16C">16c</A> Jahnson SM. Petrassi HM. Palaninathan SK. Mohamedmohaideen NN. Purkey HE. Nichols C. Chiang KP. Walkup T. Sacchettini JC. Sharpless KB. Kelly JW. J. Med. Chem. 2005, 48: 1576

<A NAME="RZ02510SS-16D">16d</A> Goda H. Ihara H. Hirayama C. Sato M. Tetrahedron Lett. 1994, 35: 1565

<A NAME="RZ02510SS-17">17</A> Bittner S. Grinberg S. J. Chem. Soc., Perkin Trans. 1 1976, 1708

<A NAME="RZ02510SS-18A">18a</A> Larock RC. Comprehensive Organic Transformations 2nd ed.: Wiley; New York: 1999.

<A NAME="RZ02510SS-18B">18b</A> Rabinowitz R. Marcus R. J. Am. Chem. Soc. 1962, 84: 1312

<A NAME="RZ02510SS-18C">18c</A> Desai NB. McKelvie N. Ramirez F. J. Am. Chem. Soc. 1962, 84: 1745

<A NAME="RZ02510SS-18D">18d</A> Fieser LF. Fieser M. In Reagents for Organic Synthesis Vol. 3: Wiley; New York: 1972. p.320

<A NAME="RZ02510SS-18E">18e</A> Gadogan JIG. Mackie RK. Chem. Soc. Rev. 1974, 3: 87

<A NAME="RZ02510SS-19A">19a</A> Appel R. Angew. Chem., Int. Ed. Engl. 1975, 14: 801

<A NAME="RZ02510SS-19B">19b</A> Årstad E. Barrett AGM. Hopkins BT. Köbberling J. Org. Lett. 2002, 4: 1975

<A NAME="RZ02510SS-19C">19c</A> Snyder EI. J. Org. Chem. 1972, 37: 1466

<A NAME="RZ02510SS-19D">19d</A> Aneja R. Davies AP. Knaggs JA. Tetrahedron Lett. 1974, 15: 67

<A NAME="RZ02510SS-20">20</A> Brett D. Dowine IM. Lee JB. J. Org. Chem. 1967, 32: 855

<A NAME="RZ02510SS-21">21</A> Ramaiah M. J. Org. Chem. 1985, 50: 4991

<A NAME="RZ02510SS-22">22</A> Barry CN. Evans SA. Tetrahedron Lett. 1983, 24: 661

<A NAME="RZ02510SS-23">23</A> Robinson PL. Barry CN. Bass SW. Jarvis SE. Evans SA. J. Org. Chem. 1983, 48: 5396

<A NAME="RZ02510SS-24A">24a</A> Kim JN. Chung KH. Pyn EK. Synth. Commun. 1990, 20: 2785

<A NAME="RZ02510SS-24B">24b</A> Yamato E. Sugasawa S. Tetrahedron Lett. 1970, 11: 4383

<A NAME="RZ02510SS-25A">25a</A> Barstow LE. Hruby VJ. J. Org. Chem. 1971, 36: 1305

<A NAME="RZ02510SS-25B">25b</A> Lee JB. J. Am. Chem. Soc. 1966, 88: 3440

<A NAME="RZ02510SS-26A">26a</A> Yang Y.-H. Shi M. Tetrahedron 2006, 62: 2420

<A NAME="RZ02510SS-26B">26b</A> Yang Y.-H. Shi M. Tetrahedron Lett. 2005, 46: 6285

<A NAME="RZ02510SS-26C">26c</A> Miller MJ. Mattingly PG. Morrison MA. Kerwin JF. J. Am. Chem. Soc. 1980, 102: 7026

<A NAME="RZ02510SS-26D">26d</A> Wang Z. Wan W. Jiang H. Hao J. J. Org. Chem. 2007, 72: 9364

<A NAME="RZ02510SS-27">27</A> Soltani Rad MN. Khalafi-Nezhad A. Behrouz S. Asrari Z. Behrouz M. Amini Z. Synthesis 2009, 3067

<A NAME="RZ02510SS-28">28</A> Buck JS. Ide WS. Org. Synth., Coll. Vol. II John Wiley & Sons; London: 1943. p.622

<A NAME="RZ02510SS-29">29</A> Smith PAS. Robertson JE. J. Am. Chem. Soc. 1962, 84: 1197

<A NAME="RZ02510SS-30">30</A> Buehler E. J. Org. Chem. 1967, 32: 261

<A NAME="RZ02510SS-31">31</A> Smith SG. Milligan DV. J. Am. Chem. Soc. 1968, 90: 2393 ; and references cited therein