86309-26-4Relevant academic research and scientific papers
Hydrostannation of conjugated enynes
Cochran,Leusink,Noltes
, p. 1099 - 1105 (2008/10/08)
Hydrostannation of three conjugated enynes is reported. The reaction was found to be catalyzed by AIBN and inhibited by galvinoxyl. The addition of trimethyltin hydride takes place preferentially at the triple bond. The initial product is one of anti addition. However, extensive isomerization, catalyzed by trimethyltin radicals, occurs at both double bonds of the dienyl system, resulting in a mixture of geometrical isomers. In each case the thermodynamically more stable isomer was the predominant product. It was also observed that trimethyltin radicals cause isomerization of the enyne prior to addition. Diaddition products were found for two of the three enynes, but telomers were absent. 1H NMR data are reported for both mono- and diaddition products.
