171856-87-4Relevant academic research and scientific papers
First evidence for the formation of a geminal dizinc carbenoid: A highly stereoselective synthesis of 1,2,3-Substituted cyclopropanes
Charette, Andre B.,Gagnon, Alexandre,Fournier, Jean-Francois
, p. 386 - 387 (2002)
Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 °C. This reagent was shown to be effective in the cyclopropanation of butenediol derivatives to generate
Regioselective and Stereospecific Copper-Catalyzed Deoxygenation of Epoxides to Alkenes
Yu, Jingxun,Zhou, Yu,Lin, Zhenyang,Tong, Rongbiao
supporting information, p. 4734 - 4737 (2016/09/28)
Two copper salts (Cu(CF3CO2)2 and IMesCuCl) were identified as earth-abundant, inexpensive, but effective metal catalysts together with diazo malonate for chemo-/regioselective and stereospecific deoxygenation of various epoxides with tolerance of common functional groups (alkene, ketone, ester, p-methoxybenzyl, benzyl, tert-butyldimethylsilyl, and triisopropylsilyl). In particular, the unprecedented regioselectivity allowed for the first time monodeoxygenation of diepoxides to alkenyl epoxides. Density functional theory mechanistic studies showed that the deoxygenation occurred by collapsing the free ylide, unfavoring the possible intuitive pathway via cycloreversion of possible oxetane.
Regiochemical control of the ring opening of 1:2-epoxides by means of chelating processes. 10. Synthesis and ring opening reactions of mono- and difunctionalized cis and trans aliphatic oxirane systems
Azzena, Francesca,Calvani, Federico,Crotti, Paolo,Gardelli, Cristina,Macchia, Franco,Pineschi, Mauro
, p. 10601 - 10626 (2007/10/02)
The regiochemical outcome of the ring opening of 1:2-epoxides through chelation processes assisted by metal ions, was verified in mono- and difunctionalized aliphatic oxirane systems bearing the heterofunctionality (OR) in an homoallylic and/or allylic relationship to the oxirane ring. The effect of the distance of the OR functionality from the oxirane ring and of the type of protective group on the regiochemical outcome of these systems is examined. In some cases, the use of LiClO4 or Mg(ClO4)2 as the promoting metal salt makes it possible the obtainment of a nice regioalternating process.
