Photoinduced electron transfer reactions of benzyl phenyl sulfides promoted by 9,10-dicyanoanthracene
1997; Elsevier BV; Volume: 53; Issue: 12 Linguagem: Inglês
10.1016/s0040-4020(97)00119-1
ISSN1464-5416
AutoresEnrico Baciocchi, Cristina Crescenzi, Osvaldo Lanzalunga,
Tópico(s)Synthesis and Biological Evaluation
ResumoThe photoinduced oxidation of benzyl phenyl sulfides 1–3 has been investigated in MeCN using 9,10-dicyanoanthracene as sensitizer in the presence of O2. In this reaction a sulfide radical cation is formed, which undergoes one or more of the three main reaction pathways opened to these species: CS bond cleavage, CH 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 O2 in this respect are discussed.
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