25573-65-3Relevant academic research and scientific papers
5-Exo versus 6-Endo cyclization of primary aminyl radicals: An experimental and theoretical investigation
Liu, Feng,Liu, Kun,Yuan, Xinting,Li, Chaozhong
, p. 10231 - 10234 (2008/09/17)
(Chemical Equation Presented) The cyclization of neutral primary pent-4-enylaminyl radicals was investigated experimentally and theoretically. Unlike the corresponding secondary aminyl radicals, primary pent-4-enylaminyl radicals underwent efficient cyclization to afford the pyrrolidine and/or piperidine products in good to high yields. While the simple pent-4-enylaminyl radical gave predominately the 5-exo cyclization product, 4-chloropent-4- enylaminyl radicals led to the formation of the corresponding 6-endo cyclization products in excellent regioselectivity. Theoretical calculations revealed that the 5-exo cyclization rate of primary aminyl radicals is about 3-4 orders of magnitude higher than that of secondary aminyl radicals.
