1399256-04-2Relevant articles and documents
Synchronized aromaticity as an enthalpic driving force for the aromatic cope rearrangement
Babinski, David J.,El Arba, Marie,Frantz, Doug E.,Bao, Xiaoguang,Chen, Bo,Hrovat, David A.,Borden, Weston Thatcher
, p. 16139 - 16142,4 (2012)
We report herein experimental and theoretical evidence for an aromatic Cope rearrangement. Along with several successful examples, our data include the first isolation and full characterization of the putative intermediate that is formed immediately after the initial [3,3] sigmatropic rearrangement. Calculations at the B3LYP/6-31G(d) level of theory predict reaction energy barriers in the range 22-23 kcal/mol for the [3,3]-rearrangement consistent with the exceptionally mild reaction conditions for these reactions. The experimental and computational results support a significant enthalpic contribution of the concomitant pyrazole ring formation that serves as both a kinetic and thermodynamic driving force for the aromatic Cope rearrangement.
Ru(II)-Catalyzed Synthesis of Substituted Furans and Their Conversion to Butenolides
El Arba, Marie,Dibrell, Sara E.,Meece, Frederick,Frantz, Doug E.
, p. 5886 - 5888 (2018)
The synthesis of densely functionalized trisubstituted and tetrasubstituted furans via a novel Ru(II)-catalyzed intramolecular cyclization of vinyl diazoesters is reported. The synthetic utility of these furans is further demonstrated through a simple aci
