231935-01-6Relevant academic research and scientific papers
Borontribromide-mediated C-C bond formation in cyclic ketones: A transition metal free approach
Ahmad, Imran,Pathak, Vinay,Vasudev, Prema G.,Maurya, Hardesh K.,Gupta, Atul
, p. 24619 - 24634 (2014/07/07)
Borontribromide (BBr3) is a well-known demethylating agent. The current investigation was focused on a new application of borontribromide as a C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. A methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of the methoxy group. MM2 steric energy calculations for the final products showed that the reaction favored the formation of exo- or endo-cyclic double bond containing products, depending upon their low MM2 steric energy in a specific frame structure, as observed in X-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a demonstrated the formation of 10a as an enantiomeric mixture, and its centre of inversion was stabilized by a set of three unique pi-pi interactions.
One-step cross-coupling reaction of functionalized alkyl iodides with aryl halides by the use of an electrochemical method
Kurono, Nobuhito,Sugita, Kazuya,Takasugi, Shingo,Tokuda, Masao
, p. 6097 - 6108 (2007/10/03)
Organozinc compounds of functionalized alkyl iodide carrying an alkoxycarbonyl, cyano or alkenyl group were prepared in high yields under mild conditions (0°C-r.t., 10min in DMF) by the reaction of iodides with an electrogenerated reactive zinc (EGZn). Cross-coupling of the organozinc compounds with various aryl halides in the presence of 5 mol% Pd(P(o- Tol)3)2Cl2 in THF gave the corresponding cross-coupled products in moderate to high yields. These cross-coupling reactions can be also achieved in one step and in one pot by the use of an electrochemical method utilizing a Pt cathode and Zn anode.
Ring enlargement of eight- and nine-membered cyclic sulfonamide derivatives in reactions with 3-amino-2H-azirines
Mihova, Tonya R.,Linden, Anthony,Heimgartner, Heinz
, p. 215 - 232 (2007/10/03)
The reactions of 3-dimethylamino-2H-azirines (1) with 3,4,5,6- tetrahydro-8,9-dimethoxy-2H-1,2-benzothiazocin-3-one 1,1-dioxide (6a) in acetonitrile gave the correspondingly substituted 3-dimethylamino- 4,5,6,7,8,9-hexahydrobenzo-1-thia-2,5-diazacyclounde
