Photoinduced electron transfer reactions of benzyl phenyl sulfides promoted by 9,10-dicyanoanthracene

被引:66
作者
Baciocchi, E [1 ]
Crescenzi, C [1 ]
Lanzalunga, O [1 ]
机构
[1] CNR,CTR STUDIO MECCANISMI REAZ,I-00185 ROME,ITALY
关键词
D O I
10.1016/S0040-4020(97)00119-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The photoinduced oxidation of benzyl phenyl sulfides 1-3 has been investigated in MeCN using 9,10-dicyanoanthracene as sensitizer in the presence of O-2. In this reaction a sulfide radical cation is formed, which undergoes one or more of the three main reaction pathways opened to these species: C-S bond cleavage, C-H bond cleavage and S-oxidation. The former route (leading to benzylic products) was observed with all the substrates investigated, whereas the second (leading to benzaldehydes) operates only with 1 and 2. Formation of sulfoxides was found solely in the photooxidation of 1. The influence of substrate structures on the relative contribution of the three pathways as well as the role of O-2(.) in this respect are discussed. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4469 / 4478
页数:10
相关论文
共 52 条
[1]  
Akaba R, 1996, J PHYS ORG CHEM, V9, P187, DOI 10.1002/(SICI)1099-1395(199603)9:3<187::AID-POC764>3.3.CO
[2]  
2-T
[3]   CHARGE-TRANSFER PHOTOOXYGENATION OF SULFIDES IN A CRYOGENIC OXYGEN MATRIX - IR SPECTROSCOPIC OBSERVATION OF PERSULFOXIDES [J].
AKASAKA, T ;
YABE, A ;
ANDO, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) :8085-8087
[4]   DYE-PHOTOSENSITIZED AND DICYANOANTHRACENE-PHOTOSENSITIZED OXYGENATIONS OF SULFUR-COMPOUNDS - PRODUCT SELECTIVITY [J].
ANDO, W ;
NAGASHIMA, T ;
SAITO, K ;
KOHMOTO, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (04) :154-156
[5]  
[Anonymous], PHOTOINDUCED ELECT T
[6]   MEDIUM AND STRUCTURE EFFECTS ON THE ANODIC-OXIDATION OF ARYL ARYLMETHYL SULFIDES [J].
BACIOCCHI, E ;
ROL, C ;
SCAMOSCI, E ;
SEBASTIANI, GV .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5498-5502
[7]   STEREOCHEMISTRY OF THE C-S BOND-CLEAVAGE IN 1-PHENYLETHYL PHENYL SULFIDE RADICAL-CATION - EVIDENCE FOR A UNIMOLECULAR PATHWAY [J].
BACIOCCHI, E ;
FASELLA, E ;
LANZALUNGA, O ;
MATTIOLI, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07) :1071-1073
[8]  
BACIOCCHI E, 1989, GAZZ CHIM ITAL, V119, P649
[9]   THE MECHANISM OF ENZYMATIC AND BIOMIMETIC OXIDATIONS OF AROMATIC SULFIDES AND SULFOXIDES [J].
BACIOCCHI, E ;
LANZALUNGA, O ;
MARCONI, F .
TETRAHEDRON LETTERS, 1994, 35 (52) :9771-9774
[10]   Oxidation of sulfides by peroxidases. Involvement of radical cations and the rate of the oxygen rebound step [J].
Baciocchi, E ;
Lanzalunga, O ;
Malandrucco, S ;
Ioele, M ;
Steenken, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (37) :8973-8974