Oxidative cleavage of tosylhydrazones and sulfilimines = 토실히드라존과 술필이민들의 산화 분열반응

Arylperoxyseleninic acids were generated from arylseleninic acids and hydrogen peroxide in situ and found to be a good oxidizing agent of tosylhydrazone derivatives. Tosylhydrazones were found to react with the mixture of aqueous hydrogen peroxide and catalytic amount of arylseleninic acid in THF to convert into the corresponding carbonyl compounds in excellent yields under mild conditions. The o-nitrobenzeneseleninic acid is more efficient catalyst then benzeneseleninic acid for these oxidation reactions. The reaction system appears to be safe and is simple to work up. Thus, it may be promising for the deprotection of tosylhydrazone derivatives to the corresponding ketones under mild conditions. While, various sulfilimine derivativs were found to react with dinitrogen tetroxide in dry acetonitrile or THF to give the corresponding sulfoxide derivatives, in excellent yields. Dinitrogen tetroxide has been known to be self-ionized to $NO^+$ and $NO^-_3$ ion at low temperature in polar aprotic solvent. Dinitrogen tetroxide is the powerful nitrosating reagent at low temperature in acetonitrile or THF. The reaction appears to proceed via nitrosation on the nitrogen atom of S=N bond.
Advisors
Kim, Yong-Haeresearcher김용해researcher
Publisher
한국과학기술원
Issue Date
1989
Identifier
66569/325007 / 000871283
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1989.2, [ vi, 54 p. ]

URI
http://hdl.handle.net/10203/32541
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=66569&flag=t
Appears in Collection
CH-Theses_Master(석사논문)
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