Download PDF
Synthesis 2005(13): 2215-2219  
DOI: 10.1055/s-2005-872093
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Geminal Bisperoxides by Acid-Catalyzed Reaction of Acetals and Enol Ethers with tert-Butyl Hydroperoxide

Alexander O. Terent’ev*, Alexander V. Kutkin, Nikolay A. Troizky, Yuri N. Ogibin, Gennady I. Nikishin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia
Fax: +8(095)135 5328; e-Mail: alterex@yandex.ru;
Further Information

Publication History

Received 3 March 2005
Publication Date:
22 July 2005 (online)

    Permissions and Reprints All articles of this category

Abstract

A new efficient procedure was developed for the synthesis of geminal bisperoxides by reaction of ketals and enol ethers with tert-butyl hydroperoxide catalyzed by protic or Lewis acids.

Key words

acetals - enol ethers - tert-butyl hydroperoxide - gem-bisperoxides

    References

  • 1 Antonovskii V. L.; In Organicheskie Perekisnye Initsiatory (in Russian) (Organic Peroxide Initiators); Khimiya: Moscow, 1972
  • 2a Organic Peroxides   Vol. 1:  Swern D. Wiley; New York: 1970. 
    Google Scholar
  • 2b Organic Peroxides   Vol. 2:  Swern D. Wiley; New York: 1971. 
    Google Scholar
  • 2c Organic Peroxides   Vol. 3:  Swern D. Wiley; New York: 1972. 
    Google Scholar
  • 3 The Chemistry of Peroxides   Patai S. Wiley; New York; Interscience Publishers: Chichester: 1983. 
    Google Scholar
  • 4 Kropf H. In Houben-Weyl, Methoden der Organischen Chemie   Vol. E13:  Georg Thieme Verlag; Stuttgart: 1988. 
    Google Scholar
  • 5 Sawaki Y. In Organic Peroxides   Ando W. Wiley-VCH; New York: 1992.  p.450 
    Google Scholar
  • 6 Peroxide Chemistry   Adam W. Wiley-VCH; New York: 2000. 
    Google Scholar
  • 7 Hamada Y. Tokuhara H. Masuyama A. Nojima M. Kim H.-S. Ono K. Ogura N. Wataya Y. J. Med. Chem.  2002,  45:  1374 
    CrossrefGoogle Scholar
  • 8 McCullough KJ. Ito T. Tokuyasu T. Masuyama A. Nojima M. Tetrahedron Lett.  2001,  42:  5529 
    CrossrefGoogle Scholar
  • 9 Dickey FH. Rust FF. Vaughan WE. J. Am. Chem. Soc.  1949,  71:  1433 
    Google Scholar
  • 10 Kharash M. Sosnovsky G. J. Org. Chem.  1958,  23:  1322 
    CrossrefGoogle Scholar
  • 11 Nazarova ZF. Bocharova YE. Batog AE. Romantsevich MK. Zh. Org. Khim.  1966,  2:  259 ; Chem. Abstr.  1966,  65:  2116 
    Google Scholar
  • 12 Komai T, Matsushima M, and Nakajima T. inventors; Ger. Offen.,  2546743.  ; Chem. Abstr. 1976, 85, 63706
  • 13 Mukaiyama T. Miyoshi N. Kato J. Ohshima M. Chem. Lett.  1986,  1385 
    Google Scholar
  • 14 Sugihara Y. Watanabe Y. Kumura H. Nakamura T. Suyama S. Sawaki Y. Bull. Chem. Soc. Jpn.  1992,  65:  664 
    CrossrefGoogle Scholar
  • 15 Matsuyama K. Kimura H. J. Org. Chem.  1993,  58:  1766 
    CrossrefGoogle Scholar
  • 16 Weygand C. Hilgetag G. Organischen-Chemischen Experimentierkunst   Johann Ambrosius Barth Verlag; Leipzig: 1964. 
    Google Scholar
  • 17 Becker HGO. Berger W. Domschke G. Organikum   VEB Deutscher Verlag der Wissenschaften; Berlin: 1964. 
    Google Scholar
  • 18 Meerwein H. In Houben-Weyl, Methoden der Organischen Chemie   Vol. VI/3:  Muller E. Georg Thieme Verlag; Stuttgart: 1965.  p.199 
    Google Scholar
  • 19 Terent’ev AO. Kutkin AV. Platonov MM. Vorontsov II. Antipin MY. Ogibin YN. Nikishin GI. Izv. Akad. Nauk, Ser. Khim.  2004,  650 ; Russ. Chem. Bull. Int. Ed., 2004, 681
    Google Scholar
  • 20 Dictionary of Organic Compounds   Vol. 1-7, 5th ed.:  Chapman & Hall; New York / Liverpool / Toronto: 1982-1988.  Suppl. 1-6.
    Google Scholar
  • 21 Matsuyama K. Kumura H. J. Org. Chem.  1993,  58:  1766 
    CrossrefGoogle Scholar