An Efficient Oxidation of Element-Containing
Propargyl Alcohols and Acetylenic γ-Diols by
2-Iodoxybenzoic Acid (IBX)

Irina A. Novokshonova; Vladimir V. Novokshonov; Alevtina S. Medvedeva

doi:10.1055/s-0028-1087225

PAPER

An Efficient Oxidation of Element-Containing Propargyl Alcohols and Acetylenic γ-Diols by 2-Iodoxybenzoic Acid (IBX)

Irina A. Novokshonova, Vladimir V. Novokshonov, Alevtina S. Medvedeva*
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia
Fax: +7(3952)419346; e-Mail: amedved@irioch.irk.ru;

Abstract

All articles of this category

Abstract

An efficient and convenient procedure for the oxidation of acetylenic alcohols and diols by o-iodoxybenzoic acid (IBX) is reported. Simple heating of the corresponding alcohol with a suspension of IBX in acetone or tetrahydrofuran leads to the silicon(germanium)-containing propynals or γ-hydroxypropynals in high yields.

Key words

propargyl alcohols - acetylenic diols - oxidation - IBX - propynals

Full Text

References

1a Singer RA. Shepard MS. Carreira EM. Tetrahedron 1998, 54: 7025

1b Oguni N. Satoh N. Fujii H. Synlett 1995, 1043

2 Loh T.-P. Ho DS.-C. Xu K.-C. Sim K.-Y. Tetrahedron Lett. 1997, 38: 865

3 Wan Z. Nelson SG. J. Am. Chem. Soc. 2000, 122: 10470

4a Massey EH. Kitchell BS. Martin LD. Gerzon K. J. Med. Chem. 1974, 17: 105

4b Toshima H. Aramaki H. Ichihara A. Tetrahedron Lett. 1999, 40: 3587

5 Baker JR. Thominet O. Britton H. Caddick S. Org. Lett. 2007, 9: 45

6a Agami C. Couty F. Mathieu H. Tetrahedron Lett. 1996, 37: 4001

6b Novokshonova IA. Medvedeva AS. Afonin AV. Safronova LP. Russ. J. Org. Chem. (Engl. Transl.) 2004, 40: 1214

6c Medvedeva AS. Novokshonova IA. Afonin AV. Safronova LP. Russ. J. Org. Chem. (Engl. Transl.) 2005, 41: 1708

7 Nichols CS. Cromartie TH. Biochem. Biophys. Res. Commun. 1980, 97: 216

8 Huang H. Panek JS. Org. Lett. 2001, 3: 1693

9 Awasthi AK. Boys ML. Cain-Janicki KJ. Colson P.-J. Doubleday WW. Duran JE. Farid PN. J. Org. Chem. 2005, 70: 5387

10 Demina MM. Novopashin PS. Sarapulova GI. Larina LI. Smolin AS. Fundamenskii VS. Kashaev AA. Medvedeva AS. Russ. J. Org. Chem. (Engl. Transl.) 2004, 40: 1804

11 Novokshonov VV. Novokshonova IA. Ushakov IA. Medvedeva AS. Chem. Heterocycl. Compd. (Engl. Transl.) 2006, 42: 1492

12 Medvedeva AS. Khatashkeev AV. Mareev AV. Afonin AV. Ushakov IA. Russ. J. Org. Chem. (Engl. Transl.) 2005, 41: 1706

13 Mareev AV. Tikhonov AV. Afonin AV. Ushakov IA. Medvedeva AS. Russ. J. Org. Chem. (Engl. Transl.) 2005, 41: 1397

14 Mareev AV. Medvedeva AS. Khatashkeev AV. Afonin AV. Mendeleev Commun. 2005, 15: 263

15a Milgrom LR. Yahioglu G. Tetrahedron Lett. 1996, 37: 4069

15b Plater MJ. Aiken S. Bourhill G. Tetrahedron 2002, 58: 2415

16 Medvedeva AS. Demina MM. Novopashin PS. Sarapulova GI. Afonin AV. Mendeleev Commun. 2002, 110

17 Fatiadi AJ. Synthesis 1976, 133

18a Corey EJ. Schmidt G. Tetrahedron Lett. 1979, 20: 399

18b Piancatelli G. Scettri A. D’Auria M. Synthesis 1982, 245

19a Mancuso AJ. Swern D. Synthesis 1981, 165

19b Luca LD. Giacomelli G. Porcheddu A. J. Org. Chem. 2001, 66: 7907

20 Han Z. Shinokubo H. Oshima K. Synlett 2001, 1421

21 Maeda Y. Kakiuchi N. Matsumura S. Nishimura T. Uemura S. Tetrahedron Lett. 2001, 42: 8877

22 Medvedeva AS. Safronova LP. Chichkareva GG. Voronkov MG. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1976, 25: 107

23 Vereshchagin LI. Lipovich TV. Gainylina SR. Podskrebysheva SA. Okhapkina LL. Vorob’eva VU. Latyshev VP. Zh. Org. Khim. 1972, 8: 1129 ; Chem. Abstr. 1972, 77, 100983f

24 Serrat X. Cabarrocas G. Rafel S. Ventura M. Linden A. Villagordo JM. Tetrahedron: Asymmetry 1999, 10: 3417

25 Demina MM. Medvedeva AS. Protsuk NI. Vyazankin NS. Zh. Obshch. Chem. 1978, 48: 1563 ; Chem. Abstr. 1978, 89, 163691c

26 Givan GV. Master of Science Miami University; USA: 2003. p.120 ; http://www.ohiolink.edu/etd/view.cgi?miami1071175859

27 Zhdankin VV. Curr. Org. Synth. 2005, 2: 121

28a Nicolaou KC. Montagnon T. Baran PS. Zhong Y.-L. J. Am. Chem. Soc. 2002, 124: 2245

28b De Munari S. Frigerio M. Santagostino M. J. Org. Chem. 1996, 61: 9272

29 Frigerio M. Santagostino M. Tetrahedron Lett. 1994, 35: 8019

30 Frigerio M. Santagostino M. Sputore S. Palmisano G. J. Org. Chem. 1995, 60: 7272

31 Yokokawa F. Shioiri T. Tetrahedron Lett. 2002, 43: 8673

32 Thottumkara AP. Bowsher MS. Vinod TK. Org. Lett. 2005, 7: 2933

33 Dess DB. Martin JC. J. Am. Chem. Soc. 1991, 113: 7277

34 More JD. Finney NS. Org. Lett. 2002, 4: 3001

35 Surendra K. Krishnaveni NS. Reddy MA. Nageswar YVD. Rao KR. J. Org. Chem. 2003, 68: 2058

36a Barrett AGM. Hamprecht D. Ohkudo M. J. Org. Chem. 1997, 62: 9376

36b Zeng J. Deng G. Yu W. Li D. Bioorg. Med. Chem. Lett. 2006, 16: 1445

37 Legoupy S. Crévisy C. Guillemin J.-C. Grée R. J. Organomet. Chem. 1998, 567: 75