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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 23, Number 1
BKCSDE 23(1)
January 20, 2002 

New Mechanism for the Reaction of Thianthrene Cation Radical Perchlorate with tert-Butyl Peroxide
Bo Kyung Park, Chang Kook Sohn, Wang Keun Lee
Thianthrene cation radical, t-Butyl peroxide, B3LYP and CBS-4 methods.
A new reaction mechanism is proposed for the reaction of thianthrene cation radical perchlorate (Th ClO4- ) and tert-butyl peroxide in acetonitrile at room temperature on the basis of experimental and theoretical results. Rapid C-O bond rupture instead of O-O bond cleavage was observed by a good peroxy radical trapping agent, thianthrene cation radical. Products were N-tert-butyl acetamide, thianthrene 5-oxide (ThO), thianthrene 5,5-dioxide (SSO2), and thianthrene (Th). Thianthrene 5,10-dioxide (SOSO) was not obtained. A comparative computational study of the cation radical of tert-butyl peroxide is made by using B3LYP and CBS-4. The computational results are helpful to explain the reaction mechanism.
103 - 106
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