Download PDF
Synlett 2005(10): 1509-1520  
DOI: 10.1055/s-2005-869847
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Toshiaki Murai*
Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
e-Mail: mtoshi@cc.gifu-u.ac.jp;
Further Information

Publication History

Received 1 November 2004
Publication Date:
12 May 2005 (online)

    Permissions and Reprints All articles of this category

Abstract

This review describes the synthesis and reactions of selenothioic acid S-esters and diselenoic acid esters. Synthetic work with these substances has provided observations, which have led to a proposal about factors that effect their stability. A survey shows that aliphatic derivatives of selenothioic acid S-esters, although being stable compounds, are highly reactive with various electrophilic and nucleophilic reagents. In addition, α-protons in these esters have high acidities. Studies have shown that the chemistry of these esters can be utilized in the synthesis of new types of organoselenium compounds.

1 Introduction

2 Synthesis

2.1 Synthesis via Selenoketene Intermediates

2.2 Synthesis via Selenoic Acid O-Esters

3 Spectroscopic Properties

4 Reactions

4.1 Electrophilic Reactions

4.2 Nucleophilic Reactions

4.3 Concerted Reactions

4.4 Reactions via Eneselenolates

5 Summary

Key words

selenothioic acid S-esters - diselenoic acid esters - organoselenium compounds - selenium-containing heterocycles

    References

  • 1a Murai T. Kato S. In Topics in Current Chemistry   Vol 208:  Wirth T. Springer-Verlag; Berlin: 2000.  p.177 
    Google Scholar
  • 1b Grobe J. Le Van D. J. Fluorine Chem.  2004,  125:  801 
    Google Scholar
  • 2 Tokitoh N. Okazaki R. Polish J. Chem.  1998,  72:  971 
    Google Scholar
  • 3a Guziec FS. Guziec LJ. In Organoselenium Chemistry: A Practical Approach   Back TG. Oxford University Press; UK: 1999.  p.193 
    Google Scholar
  • 3b Guziec LJ. Guziec FS. In Comprehensive Organic Functional Group Transformations   Vol. 3:  Katritzky AR. Taylor RJK. Elsevier; Oxford U.K.: 2005.  p.397 
    Google Scholar
  • For recent examples of the generation and reaction of selenoaldehydes and -ketones:
  • 4a Okuma K. Kubota T. Tetrahedron Lett.  2001,  42:  3881 
    CrossrefGoogle Scholar
  • 4b Zhou A. Segi M. Nakajima T. Tetrahedron Lett.  2003,  44:  1179 
    CrossrefGoogle Scholar
  • 4c Okuma K. Kubo K. Yokomori Y. Heterocycles  2003,  60:  299 
    CrossrefGoogle Scholar
  • 4d Segi M. Yuki Gosei Kagaku Kyokaishi  2003,  61:  661 
    CrossrefGoogle Scholar
  • 4e Okuma K. Kojima K. Oyama K. Kubo K. Shioji K. Eur. J. Org. Chem.  2004,  820 
    CrossrefGoogle Scholar
  • 5a Wu R. Barr ME. Hernandez GO. Charles CC. Silks LA. Recent Res. Dev. Org. Bioorg. Chem.  1998,  2:  29 
    Google Scholar
  • 5b Wu R. Hernandez G. Dunlap RB. Odom JD. Martinez RA. Silks LA. Trends Org. Chem.  1998,  7:  105 
    Google Scholar
  • 5c Bricklebank N. Recent Res. Dev. Inorg. Organomet. Chem.  2001,  1:  25 
    Google Scholar
  • 5d Guziec LJ. Guziec FS. In Comprehensive Organic Functional Group Transformations   Vol. 6:  Katritzky AR. Taylor RJK. Elsevier; Oxford, U.K.: 2005.  p.573 
    Google Scholar
  • For recent examples of the syntheses of selenourea, seleno-, selenothio-, and diseleno-carbamates:
  • 6a Koketsu M. Fukuta Y. Ishihara H. J. Org. Chem.  2002,  67:  1008 
    CrossrefGoogle Scholar
  • 6b Koketsu M. Takakura N. Ishihara H. Synth. Commun.  2002,  32:  3075 
    CrossrefGoogle Scholar
  • 6c Zhou Y. Denk MK. Tetrahedron Lett.  2003,  44:  1295 
    CrossrefGoogle Scholar
  • 6d Keil D. Hartmann H. Synthesis  2004,  15 
    CrossrefGoogle Scholar
  • 6e Fernandez-Bolanos JG. Lopez O. Ulgar V. Maya I. Fuentes J. Tetrahedron Lett.  2004,  45:  4081 
    CrossrefGoogle Scholar
  • For recent examples of the synthesis of selenoamides:
  • 7a Murai T. Aso H. Kato S. Org. Lett.  2002,  4:  1407 
    Google Scholar
  • 7b Koketsu M. Okayama Y. Aoki H. Ishihara H. Heteroat. Chem.  2002,  13:  195 
    Google Scholar
  • 7c Hua-Rong Z. Qing-Sen Y. Chinese J. Chem.  2002,  20:  891 
    Google Scholar
  • 7d Geisler K. Jacobs A. Kunzler A. Mathes M. Girrleit I. Zimmermann B. Bulka E. Pfeiffer W.-D. Langer P. Synlett  2002,  1983 
    Google Scholar
  • 7e Koketsu M. Takenaka Y. Ishihara H. Heteroat. Chem.  2003,  14:  106 
    Google Scholar
  • 7f Mutoh Y. Murai T. Org. Lett.  2003,  5:  1361 
    Google Scholar
  • 7g Murai T. Ishizuka M. Suzuki A. Kato S. Tetrahedron Lett.  2003,  44:  1343 
    Google Scholar
  • 7h Murai T. Fujishima A. Iwamoto C. Kato S. J. Org. Chem.  2003,  68:  7979 
    Google Scholar
  • 7i Bethke J. Karaghiosoff K. Wessjohann LA. Tetrahedron Lett.  2003,  44:  6911 
    Google Scholar
  • 7j Saravanan V. Mukherjee C. Das S. Chandrasekaran S. Tetrahedron Lett.  2004,  45:  681 
    Google Scholar
  • 7k Murai T. Mini-Rev. Org. Chem.  2004,  1:  279 
    Google Scholar
  • 7l Moore AJ. In Comprehensive Organic Functional Group Transformations   Vol. 5:  Katritzky AR. Taylor RJK. Elsevier; Oxford, U.K.: 2005.  p.519 
    Google Scholar
  • 7m Flynn C. Haughton L. In Comprehensive Organic Functional Group Transformations   Vol. 5:  Katritzky AR. Taylor RJK. Elsevier; Oxford, U.K.: 2005.  p.571 
    Google Scholar
  • 8 Mayer R. Scheithauer S. Kunz D. Chem. Ber.  1966,  99:  1393 
    Google Scholar
  • 9a Wright SW. Tetrahedron Lett.  1994,  35:  1331 
    CrossrefGoogle Scholar
  • 9b Kanda T. Ezaka T. Murai T. Kato S. Tetrahedron Lett.  1995,  36:  2807 
    CrossrefGoogle Scholar
  • 9c Barton DHR. Fontana G. Tetrahedron  1996,  52:  11163 
    CrossrefGoogle Scholar
  • 9d Ishii A. Nakayama J. In Comprehensive Organic Functional Group Transformations   Vol. 5:  Katritzky AR. Taylor RJK. Elsevier; Oxford, U.K.: 2005.  p.459 
    CrossrefGoogle Scholar
  • 10 Collard-Charon C. Renson M. Bull. Soc. Chim. Belg.  1962,  71:  563 
    Google Scholar
  • 11 Schuijl PJW. Brandsma L. Arens LF. Recl. Trav. Chim. Pays-Bas  1966,  85:  889 
    Google Scholar
  • 12 Jensen KA. Mygind H. Nielsen PH. In Organic Selenium Compounds: Their Chemistry and Biology   Klayman DL. Günther WHH. Wiley-Interscience; New York: 1973.  p.263 
    Google Scholar
  • 13 Chu JYC, and Gunther WHH. inventors; US Patent  4013529. 
  • 14a Raubenheimer HG. Kruger GJ. Viljoen HW. J. Chem. Soc., Dalton Trans.  1985,  1963 
    CrossrefGoogle Scholar
  • 14b Raubenheimer HG. Kruger GJ. Linford L. Marais CF. Otte R. Hattingh JTZ. Lombard A. J. Chem. Soc., Dalton Trans.  1989,  1565 
    CrossrefGoogle Scholar
  • 14c Fischer H. Treier K. Troll C. Chem. Ber.  1995,  128:  1149 
    CrossrefGoogle Scholar
  • 14d Fischer H. Treier K. Troll C. Stumpf R. J. Chem. Soc., Chem. Commun.  1995,  2461 
    CrossrefGoogle Scholar
  • 15a Murai T. Kato S. Sulfur Reports  1998,  20:  397 
    Google Scholar
  • 15b Murai T. In Comprehensive Organic Functional Group Transformations   Vol. 5:  Katritzky AR. Taylor RJK. Elsevier; Oxford, U.K.: 2005.  p.493 
    Google Scholar
  • 16 Kato S. Komuro T. Kanda T. Ishihara H. Murai T. J. Am. Chem. Soc.  1993,  115:  3000 
    CrossrefGoogle Scholar
  • 17a Murai T. Hayashi A. Kanda T. Kato S. Chem. Lett.  1993,  1469 
    CrossrefGoogle Scholar
  • 17b Murai T. Kakami K. Hayashi A. Komuro T. Takada H. Fujii M. Kanda T. Kato S. J. Am. Chem. Soc.  1997,  119:  8592 
    CrossrefGoogle Scholar
  • 18 Murai T. Kakami K. Itoh N. Kanda T. Kato S. Tetrahedron  1996,  52:  2839 
    CrossrefGoogle Scholar
  • 19 Murai T. Takada H. Kakami K. Fujii M. Maeda M. Kato S. Tetrahedron  1997,  36:  12237 
    Google Scholar
  • 20a Murai T. Ogino Y. Mizutani T. Kanda T. Kato S. J. Org. Chem.  1995,  60:  2942 
    CrossrefGoogle Scholar
  • 20b Murai T. Kamoto T. Kato S. J. Am. Chem. Soc.  2000,  122:  9850 
    CrossrefGoogle Scholar
  • 21 Murai T. Mizutani T. Kanda T. Kato S. J. Am. Chem. Soc.  1993,  115:  5823 
    CrossrefGoogle Scholar
  • 22 Tani K. Murai T. Kato S. J. Am. Chem. Soc.  2002,  124:  5960 
    CrossrefGoogle Scholar
  • 23 Murai T. Mizutani T. Ogino Y. Fujiwara Y. Kato S. Phosphorus, Sulfur Silicon Relat. Elem.  1998,  136-138:  561 
    Google Scholar
  • 24a Nakayama J. Akiyama I. Sugihara Y. Phosphorus, Sulfur Silicon Relat. Elem.  1998,  136-138:  569 
    CrossrefGoogle Scholar
  • 24b Nakayama J. Akiyama I. Sugihara Y. Nishio T. J. Am. Chem. Soc.  1998,  120:  10027 
    CrossrefGoogle Scholar
  • 24c Nakayama J. Kitahara T. Sugihara Y. Sakamoto A. Ishii A. J. Am. Chem. Soc.  2000,  122:  9120 
    CrossrefGoogle Scholar
  • 25 Murai T. Takada H. Kanda T. Kato S. Tetrahedron Lett.  1994,  35:  8817 
    CrossrefGoogle Scholar
  • 26 Murai T. Takada H. Kanda T. Kato S. Chem. Lett.  1995,  1057 
    Google Scholar
  • For recent reviews, see:
  • 27a Metzner P. Synthesis  1992,  1185 
    CrossrefGoogle Scholar
  • 27b Majumdar KC. Ghosh S. Ghosh M. Tetrahedron  2003,  59:  7251 
    CrossrefGoogle Scholar
  • 27c Castro AMM. Chem. Rev.  2004,  104:  2939 
    CrossrefGoogle Scholar
  • 28a Vallée Y. Worrell M. J. Chem. Soc., Chem. Commun.  1992,  1680 
    CrossrefGoogle Scholar
  • 28b Brandsma L. Morkved EH. Bjorlo O. Potapov VA. Amosova SV. Sulfur Lett.  2000,  23:  215 
    CrossrefGoogle Scholar
  • 28c Stefani H. Petragnani N. Ascenso MFC. Zeni G. Synth. Commun.  2003,  33:  2161 
    CrossrefGoogle Scholar
  • 29 Murai T. Fujii M. Kanda T. Kato S. Chem. Lett.  1996,  877 
    Google Scholar
  • 30 Murai T. Maeda M. Matsuoka F. Kanda T. Kato S. Chem. Commun.  1996,  1461 
    CrossrefGoogle Scholar
  • 31 Casar Z. Maréchal AM.-L. Lorcy D. New J. Chem.  2003,  27:  1622 
    CrossrefGoogle Scholar
  • 32 Murai T. Mizutani T. Kanda T. Kato S. Heteroat. Chem.  1995,  6:  241 
    CrossrefGoogle Scholar
  • 33a Murai T. Izumi C. Kato S. Chem. Lett.  1999,  105 
    CrossrefGoogle Scholar
  • 33b Murai T. Izumi C. Itoh T. Kato S. J. Chem. Soc., Perkin Trans. 1  2000,  917 
    CrossrefGoogle Scholar
  • 34 Brown GA. Anderson KM. Murray M. Gallagher T. Hales NJ. Tetrahedron  2000,  56:  5579 
    CrossrefGoogle Scholar
  • 35 Murai T. Fujii M. Kato S. Chem. Lett.  1997,  545 
    CrossrefGoogle Scholar
  • 36 Murai T. Endo H. Ozaki M. Kato S. J. Org. Chem.  1999,  64:  2130 
    CrossrefGoogle Scholar
  • 37a Murai T. Hayakawa S. Kato S. Chem. Lett.  2000,  368 
    Google Scholar
  • 37b Murai T. Hayakawa S. Kato S. J. Org. Chem.  2001,  66:  8101 
    Google Scholar
  • 37c Murai T. Hayakawa S. Miyazaki Y. Kato S. Phosphorus, Sulfur Silicon Relat. Elem.  2001,  172:  111 
    Google Scholar
  • 38 Murai T. Kondo T. Kato S. Heteroat. Chem.  2004,  15:  187 
    CrossrefGoogle Scholar