
TY  - JOUR
A1  - Aldabbagh, Fawaz 
A1  - Busfield, W. Ken 
A1  - Jenkins, Ian D. 
T1  - The Reactivity of Sulfur-Centred Radicals towards TMIO (1,1,3,3-Tetramethyl-2,3-dihydroisoindol-2-yloxyl). A New Type of Radical Fragmentation Reaction
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2001
VL  - 54
IS  - 5
SP  - 313
EP  - 318
KW  - 
UR  - https://doi.org/10.1071/CH01100 
N2  - The thiyl radicals derived from 2-mercaptoethanol and thiophenol were found to undergo a complex series of reactions with 1,1,3,3-tetramethyl-2,3-dihydroisoindol-2-yloxyl (TMIO). Thus, treatment of 2-mercaptoethanol with di-t-butyl peroxyoxalate (DTBPO) in the presence of TMIO produced two N&#8211;S compounds&#8212;a sulfoxamide and a sufonamide&#8212;not the expected N&#8211;O&#8211;S adduct. The reaction between thiophenol and TMIO, which proceeded at a reasonable rate in the absence of DTBPO, produced 1,1,3,3-tetramethyl-2,3-dihydroisoindolin and its corresponding phenylsulfoxamide, diphenyl disulfide, phenylsulfinic acid, and 1,1,3,3-tetramethyl-2,3-dihydroisoindol-2-ylphenylsulfonate (the adduct of TMIO and the phenylsulfonyl radical). The mechanism of formation of these products, and the use of TMIO for trapping S-centred radicals, are discussed. A new radical fragmentation process, which appears to be general for aminoxyl adducts of electron-rich systems, is described. 
ER  -

