title: Discovery of Deep-Seated Skeletal Rearrangements in the Photocyclizations of Some tert-Butyl-Substituted 1,2-Diarylethylenes.
abstract: The in-solution oxidative photocyclization of stilbenes to phenanthrenes is a well-known and synthetically valuable reaction. We report here our discovery that the oxidative photocyclization of several tert-butyl-substituted 1-styrylphenanthrenes resulted not only in the expected formation of tert-butyl-substituted picenes but also in the previously unknown rearrangement leading to the formation of tert-butyl-substituted pentahelicenes.
authors.affiliation: †Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Frank B
authors.initials: FB
authors.lastname: Mallory
authors.affiliation: †Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Colleen K
authors.initials: CK
authors.lastname: Regan
authors.affiliation: †Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Bohen
authors.affiliation: †Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, United States.|‡Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Clelia W
authors.initials: CW
authors.lastname: Mallory
authors.affiliation: †Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, United States.
authors.forename: Alyssa A
authors.initials: AA
authors.lastname: Bohen
authors.affiliation: ‡Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll