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Synthesis 2005(13): 2215-2219
DOI: 10.1055/s-2005-872093
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
Further Information
Received
3 March 2005
Publication Date:
22 July 2005 (online)
Publication History
Publication Date:
22 July 2005 (online)
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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
- 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. -
2b
Organic Peroxides
Vol. 2:
Swern D. Wiley; New York: 1971. -
2c
Organic Peroxides
Vol. 3:
Swern D. Wiley; New York: 1972. - 3
The Chemistry of Peroxides
Patai S. Wiley; New York; Interscience Publishers: Chichester: 1983. - 4
Kropf H. In Houben-Weyl, Methoden der Organischen Chemie Vol. E13: Georg Thieme Verlag; Stuttgart: 1988. - 5
Sawaki Y. In Organic PeroxidesAndo W. Wiley-VCH; New York: 1992. p.450 - 6
Peroxide Chemistry
Adam W. Wiley-VCH; New York: 2000. - 7
Hamada Y.Tokuhara H.Masuyama A.Nojima M.Kim H.-S.Ono K.Ogura N.Wataya Y. J. Med. Chem. 2002, 45: 1374 - 8
McCullough KJ.Ito T.Tokuyasu T.Masuyama A.Nojima M. Tetrahedron Lett. 2001, 42: 5529 - 9
Dickey FH.Rust FF.Vaughan WE. J. Am. Chem. Soc. 1949, 71: 1433 - 10
Kharash M.Sosnovsky G. J. Org. Chem. 1958, 23: 1322 - 11
Nazarova ZF.Bocharova YE.Batog AE.Romantsevich MK. Zh. Org. Khim. 1966, 2: 259 ; Chem. Abstr. 1966, 65: 2116 - 12
Komai T,Matsushima M, andNakajima T. inventors; Ger. Offen., 2546743. ; Chem. Abstr. 1976, 85, 63706 - 13
Mukaiyama T.Miyoshi N.Kato J.Ohshima M. Chem. Lett. 1986, 1385 - 14
Sugihara Y.Watanabe Y.Kumura H.Nakamura T.Suyama S.Sawaki Y. Bull. Chem. Soc. Jpn. 1992, 65: 664 - 15
Matsuyama K.Kimura H. J. Org. Chem. 1993, 58: 1766 - 16
Weygand C.Hilgetag G. Organischen-Chemischen Experimentierkunst Johann Ambrosius Barth Verlag; Leipzig: 1964. - 17
Becker HGO.Berger W.Domschke G. Organikum VEB Deutscher Verlag der Wissenschaften; Berlin: 1964. - 18
Meerwein H. In Houben-Weyl, Methoden der Organischen Chemie Vol. VI/3:Muller E. Georg Thieme Verlag; Stuttgart: 1965. p.199 - 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 - 20 Dictionary of Organic Compounds Vol. 1-7, 5th ed.: Chapman & Hall; New York / Liverpool / Toronto: 1982-1988. Suppl. 1-6.
- 21
Matsuyama K.Kumura H. J. Org. Chem. 1993, 58: 1766