120569-20-2Relevant academic research and scientific papers
Catalytic Access to Alkyl Bromides, Chlorides and Iodides via Visible Light-Promoted Decarboxylative Halogenation
Candish, Lisa,Standley, Eric A.,Gómez-Suárez, Adrián,Mukherjee, Satobhisha,Glorius, Frank
supporting information, p. 9971 - 9974 (2016/07/19)
Herein is reported the catalytic, visible light-promoted, decarboxylative halogenation (bromination, chlorination, and iodination) of aliphatic carboxylic acids. This operationally-simple reaction tolerates a range of functional groups, proceeds at room temperature, and is redox neutral. By employing an iridium photocatalyst in concert with a halogen atom source, the use of stoichiometric metals such as silver, mercury, thallium, and lead can be circumvented. This reaction grants access to valuable synthetic building blocks from the large pool of cheap, readily available carboxylic acids.
Synthesis and reaction of 1-azabicyclo[3.1.0]hexane
Hayashi, Kazuhiko,Kujime, Eiko,Katayama, Hajime,Sano, Shigeki,Shiro, Motoo,Nagao, Yoshimitsu
experimental part, p. 1142 - 1146 (2010/03/31)
The effective formation of 1-azabicyclo[3.1.0]hexane (5) by treatment of 2-(bromomethyl)pyrrolidine hydrobromide (4) with n-BuLi was established, with the reaction occurring by a rational reaction pathway via the open chain transition state 8 based on int
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.
PHOTODECARBOXYLATIVE CHLORINATION OF CARBOXYLIC ACIDS VIA THEIR BENZOPHENONE OXIME ESTERS
Hasebe, Masato,Tsuchiya, Takashi
, p. 6287 - 6290 (2007/10/02)
Decarboxylative chlorination of various aromatic and aliphatic carboxylic acids is performed successfully by the photolysis of their benzophenone oxime esters in carbon tetrachloride and corresponding chloro compounds are prepared in good yields.High selective generation of the certain radical and efficiency of the stable radical precursor, benzophenone oxime ester, afford much advantage for radical chemistry.
