An unusual [4 + 4] cycloadduct from an o-quinodimethane: Characterisation and computational studies. Issue 1 (4th January 2018)

• Record Type: Journal Article
• Authors: Ramabhadran, Raghunath O.; Abdul Rahman, Mohamed Husaini bin; Collier, Steven J.; Storr, Richard C.; Bates, Roderick W.
• Is Part Of: Tetrahedron. Volume 74:Issue 1(2018)
• Page Start: 1
• Page End: 5
• Publication Date: 2018-01-04
• Subjects: Cycloaddition -- o-quinodimethane -- Claisen rearrangement; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.10.076
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Trapping of a pyrimidinone-derived o -quinodimethane with tetraphenylcyclopentadienone gives a mixture of the [4 + 2] and formal [4 + 4] adducts. Computational studies show that the latter arises by a sequence of [4 + 2] cycloaddition, homolysis, radical recombination to a spiro-tetrahydrofuran and Claisen rearrangement under the thermolytic conditions. Graphical abstract: