OXIDATION OF BENZYLTRIALKYLSTANNANES BY IODOSYLBENZENE CATALYZED BY IRON TETRAKIS (PENTAFLUOROPHENYL)PORPHYRIN CHLORIDE - POSSIBLE ROLE OF BENZYLOXY RADICALS

被引：8

作者：

BACIOCCHI, E ^{[1
]}

IOELE, M ^{[1
]}

机构：

[1] UNIV ROMA LA SAPIENZA,CTR CNR STUDI MECANNISMI REAZ,I-00185 ROME,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 17期

关键词：

D O I：

10.1021/jo00122a032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidations of some benzyltrialkylstannanes by iodosylbenzene induced by tetrakis(pentafluorophenyl)porphyrin chloride (TPFP)FeCl have been investigated. Benzaldehydes and benzyl alcohols are the main reaction products, accompanied by minor amounts of 1,2-diarylethanes and benzyl chlorides. A mechanism seems likely involving the formation of a benzyltrialkylstannane cation radical, which undergoes C-Sn bond cleavage to afford a benzyl radical. The formation of 1,2-diarylethane from this radical is straightforward, whereas it is suggested that benzyl alcohol and benzaldehyde result from the disproportionation of a benzyloxy radical, formed in a oxygen transfer reaction from iodosylbenzene to the benzyl radical. In CH2Cl2, benzyl alcohol can also be the result of hydrogen atom abstraction from the solvent by the benzyloxy radical.

引用

页码：5504 / 5508

页数：5

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