Effect of solvents on the homolytical decomposition of asymmetric dialkyl peroxides

Baj, S.; Dawid, M.

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Tytuł artykułu

Effect of solvents on the homolytical decomposition of asymmetric dialkyl peroxides

Autorzy

Baj S. , Dawid M.

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Języki publikacji

Abstrakty

The first-order decomposition rates of asymmetric cumyl propyl peroxide (CPP) in various solvents have been investigated. The differences in rates are discussed in terms of the polar character of reaction transition state. The ratio of reaction products derived from cumyloxyl radical PhC(Me)2O* (1-phenyl-l-ethanon to 2-phenylpropan-2-ol) varies significantly with solvents used.

Słowa kluczowe

peroxides homolytical decomposition effect of solvents

nadtlenki

Wydawca

West Pomeranian University of Technology. Publishing House

Czasopismo

Polish Journal of Chemical Technology

Rocznik

2000

Tom

Vol. 2, nr 2

Strony

1--3

Opis fizyczny

Bibliogr. 22 poz., tab., rys.

Twórcy

autor

Baj S.

baj@zeus.polsl.gliwice.pl

Institute of Organic Chemistry and Technology, Silesian Technical University, 44-100 Gliwice, Poland

autor

Dawid M.

Institute of Organic Chemistry and Technology, Silesian Technical University, 44-100 Gliwice, Poland

Bibliografia

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(2) Raley J.H., Rust F.F. and Vaughan W.E., Decomposition of Di-t-alkyl Peroxides. III. Kinetics in Liquid Phase, J. Am. Chem. Soc., 1948, 70, 1336.
(3) Raley J.H., Rust F.F. and Vaughan W.E., Decompositions of Di-tert-Alkyl Peroxides. I. Kinetics, J. Am. Chem. Soc., 1948, 70, 88.
(4) Huyser E.S. and Van Scoy R.M., Effects of Solvent on the Unimolecular Decomposition of t-Butyl Peroxide, J. Org. Chem., 1968, 33, 3524.
(5) Walling C. and Bristol D., On the Reality of Solvents Effects in the Decomosition of tert-Butyl Peroxide, J. Org. Chem., 1971, 36, 733.
(6) Goh S.H. and Ong S.H., Induced decomposition of tert-butyl peroxide in solution. II. Kinetic study, J. Chem. Soc. (B), 1970, 870.
(7) Walling C, Waits H.P., Milovanovc J. and Pappiaonnov C.G., Polar and Radical Paths in the Decomposition of Diacyl Peroxides, J. Am. Chem. Soc., 1970, 92, 4927.
(8) Wistuba E. and Ruchard C., Migration Apitudes of cyclic and polyeyclic bridgehead groups in the Criegee Rearrangement, Tetrahedron Lett., 1981, 22, 3389.
(9) Hiatt R., Organic Paroxides, Vol. III, Chap. I. D. Swern, (Editor), Wiley-Interscience, New York, 1972.
(10) Richardson W.H., Yelvington M.B., Andrist A. H., Ertley E.W., Smith R. S. and Johnson T.D., Thermal Decomosition of Tertiary Alkyl Peroxides. Substituent Effects in Peroxide Bond Homolysis and β Scission of Alkoxy Radicals, J. Org. Chem., 1973, 38, 4219.
(11) Matsuyama K. and Higuchi Y., Substituent Effects in the Decomposition of t-Alkyl t-Butyl Peroxides, Buli. Chem. Soc. Jpn., 1991, 64, 259.
(12) Matsuyama K., Sugiura T. and Minoshima Y, Substituent Effects of Alkyl Croup on the Decomposition of tert-Alkyl Peroxides, J.Org. Chem., 1995, 60, 5520.
(13) Matsuyama K. and Kumura H., Substituent Effects on the Decomposition of Bis(tert-butylperoxy)cycloalkanes), J. Org. Chem., 1993, 58, 1766.
(14) Baj S. and Dawid M., Kinetics of Homogenous Decomposition of Asymmetric Dialkyl Peroxides, Polish J. Chem., 1998, 72, 2151.
(15) Hendrickson W.H., Nguyen C.C., Nguyen J.T. and Simons K.T., Steric Electronic Substituent Effects in Tertiary Alkyl Peroxide Decompositions, Tetrahedron Lett., 1995, 7217.
(16) Khan Z. and Kabir-Ud-Din, Kinetics and mechanism of the reaction between dimethylformamide and chromium(YI), Intern. J. Chem. Kin., 1999, 31, 409.
(17) Williams A.L., Oberright E.A. and Brooks J.B., The Abstraction of Hydrogen Atoms from Liquid Hydrocarbons by t-Butoxy Radicals, J. Am. Chem. Soc., 1956, 78, 1190.
(18) Brooks J.H.T., Reaction of Hydrocarbon with tert-Butoxy Radicals, Trans. Faraday Soc., 1957, 53, 327.
(19) Huang R.L., Goh S.H. and Ong S.H., The Chemistry of Free Radicals, Ed. Edward Arnold Ltd, London, 1974, 188.
(20) Baj S., Study of the synthesis if mixed dialkyl peroxides from metal alkyl peroxide and alkyl halide by phase transfer catalysis, J. Mol. Catal. (A), 1996, 106, 11.
(21) Baj S., Quantinative determination of organic peroxides, Fresenius J. Anal. Chem., 1994, 350, 159.
(22) Baj S. and Kulicki Z., High-performance liquid chromatographic determination of products of autoxidation of isopropylbenzene derivatives, J. Chrom., 1991, 588, 33.

Typ dokumentu

Bibliografia

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