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Tetravinylethylene
Author(s) -
Lindeboom Erik J.,
Willis Anthony C.,
PaddonRow Michael N.,
Sherburn Michael S.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402840
Subject(s) - pericyclic reaction , stereocenter , chemistry , reactivity (psychology) , hydrocarbon , computational chemistry , ab initio , stereoselectivity , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , medicine , alternative medicine , pathology
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 CC 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.