Reacting cyclopropenones with arynes: access to spirocyclic xanthene-cyclopropene motifs.

Autor: Wallbaum J, Jones PG; †Technische Universität Braunschweig, Institut für Anorganische Chemie, Hagenring 30, 38106 Braunschweig, Germany., Werz DB
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2015 Apr 03; Vol. 80 (7), pp. 3730-4. Date of Electronic Publication: 2015 Mar 19.
DOI: 10.1021/acs.joc.5b00330
Abstrakt: A formal insertion of two aryne moieties into the carbon-oxygen double bond of cyclopropenone has been realized. Spirocyclic xanthene-cyclopropene scaffolds were obtained. Mechanistically, a sequence of a formal [2 + 2]-cycloaddition followed by electrocyclic ring opening and a terminating [4 + 2]-type cycloaddition is postulated. The use of an electron-rich aryne precursor led to ring cleavage of the cyclopropene to afford an unprecedented xanthylium salt.
Databáze: MEDLINE