Mechanistic Insights into the Stepwise Diels-Alder Reaction of 4,6-Dinitrobenzofuroxan
2012 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 14, no 1, 118-121 p.Article in journal (Refereed) Published
The stepwise Diels-Alder reaction between 1-trimethylsiloxy-1,3-butadiene and 4,6-dinitrobenzofuroxan is explored using state-of-the-art computational methods. The results support a stepwise mechanism via a persistent Intermediate, however, not the one previously reported (Lakhdar et al., Chem. Eur. J. 2007, 16,5681) but a heterocyclic adduct. The novel OFT functional M062X and the SCS-MP2 method were essential to reproduce a reasonable potential energy surface for this challenging system.
Place, publisher, year, edition, pages
2012. Vol. 14, no 1, 118-121 p.
IdentifiersURN: urn:nbn:se:kth:diva-91138DOI: 10.1021/ol202913wISI: 000298828500031ScopusID: 2-s2.0-84855483865OAI: oai:DiVA.org:kth-91138DiVA: diva2:508585
FunderSwedish Research Council
QC 201203092012-03-092012-03-082012-09-03Bibliographically approved