96843-20-8Relevant academic research and scientific papers
Tin-mediated free-radical cyclization of β-allenylbenzoyloximes
Depature, Michael,Diewok, Josef,Grimaldi, Jacques,Hatem, Jacques
, p. 275 - 280 (2007/10/03)
A set of allene-tethered benzoyloximes (5) has been treated with nBu3SnH. Depending on their substitution pattern, a wide range of compounds has been obtained. If the stannyl radical adds on the allene, the C-centred radical thus formed undergoes either a 5-exo ring closure to give the cyclopentene derivatives 7 or a 6-endo ring closure onto the N atom to give the dihydropyridines 8. If the stannyl radical adds on the benzoyl moiety, an iminyl radical is formed which leads to the 3H-pyrroles 9 and the alkylidene- pyrrolines 10. Steric effects as well as polar effects are the factors governing the reaction course.
