PHOTOOXIDATION OF SULFENIC ACID-DERIVATIVES .4. REACTIONS OF SINGLET OXYGEN WITH SULFENAMIDES

被引:28
作者
CLENNAN, EL
ZHANG, HW
机构
[1] Department of Chemistry, University of Wyoming, Laramie
关键词
D O I
10.1021/ja00120a003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reactions of singlet oxygen with nine sulfenamides are reported. A detailed kinetic study reveals that two intermediates are required on the photooxidation reaction surface. One intermediate acts as a nucleophile and the second intermediate as an electrophile in their reactions with diaryl sulfoxides and diaryl sulfides, respectively. Physical quenching is also suppressed in the sulfenamides relative to other sulfur-containing singlet oxygen substrates, The mechanism of the reaction is discussed and compared to diethyl sulfide photooxidation, and a rationale for the decreased importance of physical quenching in these substrates is presented.
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页码:4218 / 4227
页数:10
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