title: Applications of hydrogen-bond-acceptor templates to direct 'in-phase' reactivity of a diene diacid in the solid state.
abstract: The hydrogen-bond-acceptor (HBA) templates 2,3-bis(4-methylenethiopyridyl)naphthalene (2,3-nap) and 1,8-bis(4-pyridyl)naphthalene (1,8-dpn) are used to assemble (E,E)-2,5-dimethylmuconic acid (dmma) in the solid state for an intermolecular [2 + 2] photocycloaddition. Co-crystallisation of 2,3-nap with dmma affords an 1D hydrogen-bonded polymer that is photostable while 1,8-nap affords a 0D hydrogen-bonded assembly that is photoactive. The diene stacks in-phase and reacts to give a syn monocyclobutane in up to 55% yield.
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, USA.
authors.forename: Manza B J
authors.initials: MB
authors.lastname: Atkinson
authors.forename: Anatoliy N
authors.initials: AN
authors.lastname: Sokolov
authors.forename: Dejan-Krešimir
authors.initials: DK
authors.lastname: Bučar
authors.forename: S V Santhana
authors.initials: SV
authors.lastname: Mariappan
authors.forename: Martin T
authors.initials: MT
authors.lastname: Mwangi
authors.forename: Michael C
authors.initials: MC
authors.lastname: Tiedman
authors.forename: Leonard R
authors.initials: LR
authors.lastname: MacGillivray