S. Kozima, H. Fujita, T. Hitomi
Oct 1, 1980
Citations
0
Influential Citations
9
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The mechanism of the oxidative cleavage of tin–tin bonds in hexamethyldistannane (Me3SnSnMe3) and hexabutyldistannane (Bu3SnSnBu3) with several 1,4-benzoquinones was investigated. Chlorine-substituted 1,4-benzoquinones exerted higher reactivity, implying that the electron-acceptability of quinone is a factor governing the reaction. Stoichiometric treatments of chloranil with the distannanes ruled out the alleged isolation of the free radical, 4-(trimethylstannoxy)phenoxyl radical, reported by Gornwell et al. The final products were not the free radical entity but normal compounds, 1,4-bis(trimethylstannoxy)benzenes. Measurements of ESR spectra revealed the formation of the semiquinone radical anions and the subsequent formation of 4-(tributylstannoxy)phenoxyl radicals as reactive intermediates in the reaction pathway.