1713-47-9Relevant academic research and scientific papers
Computational and synthetic studies with tetravinylethylenes
Lindeboom, Erik J.,Willis, Anthony C.,Paddon-Row, Michael N.,Sherburn, Michael S.
, p. 11496 - 11507 (2014)
Computational and experimental studies offer fresh insights into the neglected tetravinylethylene class of compounds. Both the structures and the outcomes of exploratory reactions of the parent hydrocarbon are predicted and explained in detail through hig
Tetravinylethylene
Lindeboom, Erik J.,Willis, Anthony C.,Paddon-Row, Michael N.,Sherburn, Michael S.
, p. 5440 - 5443 (2014)
The first four-fold cross coupling reaction involving alkenic partners leads to the title hydrocarbon on multi-gram scale in one step from commercially available precursors. In stark contrast to its close structural relatives, tetravinylethylene is a remarkably robust, bench-stable compound. The π-bond rich hydrocarbon is shown to undergo one-pot sequences of pericyclic reactions leading to the formation of complex systems with four new rings, seven C-C bonds and ten stereocenters with a very high level of stereoselectivity. Insights into the reactivity of this and related systems is provided using the accurate composite ab initio MO G4(MP2) method. Targets very efficiently: The forgotten hydrocarbon, tetravinylethylene (TVE, scheme) is a bench-stable compound that can be synthesized in one step from commercially available starting materials. TVE is a vehicle for rapid complex molecule synthesis through one-pot sequences involving the stereoselective assembly of up to seven C-C bonds.
Nonconcerted Cope-Rearrangement? 1,2,6,7-Cyclodecatetraene Thermolysis
Roth, Wolfgang R.,Schaffers, Thomas,Heiber, Margarita
, p. 739 - 750 (2007/10/02)
From the pressure and oxygen dependence of the trapping rate a two-step mechanism for the Cope rearrangement of the title compound is deduced, its energy profile established, and the heat of formation of the intermediate diradical 3 determined.In contrast to the meso compound the rearrangement of the rac isomer proceeds by two competing processes, a concerted and a nonconcerted pathway.The different behavior of the meso and rac compound can be correlated to the boat and chair geometry of the respective transition states. Key Words: Cope rearrangement / Diradicals / Oxygen trapping / Energy well / Chemical activation
