title: Triple Benzannulation of Naphthalene via a 1,3,6-Naphthotriyne Synthetic Equivalent. Synthesis of Dibenz[a,c]anthracene.
abstract: A new synthesis of dibenzo[a,c]anthracene (4) is described that features the generation, from tetrabromo-bis-triflate 1 and phenyllithium, of a 1,3,6-naphthotriyne (2) synthetic equivalent that is trapped with 3 equiv of furan to form Diels-Alder tris-adduct 3. A subsequent two-step deoxygenation of 3 represents the first synthesis of dibenz[a,c]anthracene (4) that involves a tandem aryne Diels-Alder cycloaddition-deoxygenation strategy.
authors.affiliation: Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755-3564, United States.
authors.forename: Philip Z
authors.initials: PZ
authors.lastname: Mannes
authors.affiliation: Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755-3564, United States.
authors.forename: Evans O
authors.initials: EO
authors.lastname: Onyango
authors.affiliation: Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755-3564, United States.
authors.forename: Gordon W
authors.initials: GW
authors.lastname: Gribble