107264-25-5Relevant 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.
Rhodium-catalyzed intramolecular, anti-Markovnikov hydroamination. Synthesis of 3-arylpiperidines
Takemiya, Akihiro,Hartwig, John F.
, p. 6042 - 6043 (2007/10/03)
The intramolecular anti-Markovnikov hydroamination of 1-(3-aminopropyl)vinylarenes in the presence of a readily available rhodium catalyst to form 3-arylpiperidines is reported. In contrast to intermolecular hydroamination of vinylarenes, which occurred in high yields in the presence of rhodium catalysts containing DPEphos, the intramolecular reaction occurred in high yield in the presence of [Rh(COD)(DPPB)]BF4 as catalyst. Reactants with substituents β to the nitrogen occurred in high yield, and these reactions formed 3,5-disubstituted piperidines with high diastereomeric excess. The regiochemistry of these cyclizations contrasts with the regiochemistry of intramolecular hydroaminations catalyzed by lanthanide complexes, group III metal complexes, and platinum complexes, all of which have been reported to form cyclization products from Markovnikov addition. Copyright
PHOTOCHEMICAL GENERATION OF ALIPHATIC RADICALS FROM BENZOPHENONE OXIME ESTERS: SIMPLE SYNTHESIS OF ALKYLBENZENES AND ALKYLPYRIDINES
Hasebe, Masato,Tsuchiya, Takashi
, p. 3239 - 3242 (2007/10/02)
Photolysis of benzophenone oxime esters, prepared with aliphatic carboxylic acids and benzophenone oxime, in benzene and pyridine generates various primary, secondary and tertiary aliphatic radicals selectively, and corresponding alkylbenzenes and alkylpyridines are produced in good yields, respectively.
