A new mechanism for oxidative C-S bond cleavage during reactions of singlet oxygen with organic sulfides: Electronically dictated reaction selectivity in the persulfoxide intermediate

被引:29
作者
Toutchkine, A [1 ]
Clennan, EL [1 ]
机构
[1] Univ Wyoming, Dept Chem, Laramie, WY 82071 USA
关键词
D O I
10.1021/ja993867+
中图分类号
O6 [化学];
学科分类号
0703 ;
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页码:1834 / 1835
页数:2
相关论文
共 16 条
[1]   COOXIDATION REACTION IN THE SINGLET OXYGENATION OF CYCLIC AND BENZYLIC SULFIDES - S-HYDROPEROXYSULFONIUM YLIDE INTERMEDIATE AS A NEW EPOXIDIZING SPECIES [J].
AKASAKA, T ;
SAKURAI, A ;
ANDO, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) :2696-2701
[2]   NOVEL ADDUCTS OF SULFIDES AND 4-SUBSTITUTED 1,2,4-TRIAZOLINE-3,5-DIONES (TAD) - A SIMILARITY OF TAD AND SINGLET OXYGEN O-1(2) [J].
ANDO, W ;
ITO, K ;
TAKATA, T .
TETRAHEDRON LETTERS, 1982, 23 (38) :3909-3912
[3]  
Bonesi SM, 1999, EUR J ORG CHEM, V1999, P1723
[4]   Photosensitized oxygenation of benzyl ethyl sulfide [J].
Bonesi, SM ;
Mella, M ;
d'Alessandro, N ;
Aloisi, GG ;
Vanossi, M ;
Albini, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9946-9955
[5]  
COREY EJ, 1976, TETRAHEDRON LETT, P4263
[6]   Nucleophilic reactions at the sulfur of thiiranium and thiirenium ions. New insight in the electrophilic additions to alkenes and alkynes. Evidence for an episulfurane intermediate [J].
Fachini, M ;
Lucchini, V ;
Modena, G ;
Pasi, M ;
Pasquato, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :3944-3950
[7]   Mechanism of sulfone formation in the reaction of sulfides and singlet oxygen: Intermediacy of S-hydroperoxysulfonium ylide [J].
Ishiguro, K ;
Hayashi, M ;
Sawaki, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) :7265-7271
[8]   REACTION OF ORGANIC SULFIDES WITH SINGLET OXYGEN - A THEORETICAL-STUDY INCLUDING ELECTRON CORRELATION [J].
JENSEN, F .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6478-6487
[9]   Reaction of organic sulfides with singlet oxygen. A revised mechanism [J].
Jensen, F ;
Greer, A ;
Clennan, EL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4439-4449
[10]  
KICE JL, 1980, ADV PHYS ORG CHEM, V17, P65