title: Crossed McMurry Coupling Reactions for Porphycenic Macrocycles: Non-Statistical Selectivity and Rationalisation.
abstract: Crossed McMurry reactions of bifuran- or bithiophenedicarbaldehydes with bipyrroledicarbaldehydes have been studied for the first time. Only those porphycenic macrocycles derived from homocoupled McMurry products were formed. The results are explained by using both density functional theory and electron propagator computations to model the electron affinity of the dialdehyde starting materials. It was predicted that bifuran\bithiophene cross-coupling would indeed occur, and this was demonstrated by the first synthesis of a novel dioxa,dithio hetero-porphycenoid annulene. This approach will allow the prior identification of viable substrates for related crossed McMurry reactions.
authors.affiliation: School of EPS - Institute of Chemical Sciences, Heriot-Watt University Riccarton, Edinburgh, EH14 4AS, UK E-mail: m.j.paterson@hw.ac.uk m.w.p.bebbington@hw.ac.uk http://www.theophotochem.eps.hw.ac.uk/Home.html , http://www.hw.ac.uk/schools/engineering-physical-sciences/staff-directory/mb.htm.
authors.forename: Thomas Y
authors.initials: TY
authors.lastname: Cowie
authors.affiliation: School of EPS - Institute of Chemical Sciences, Heriot-Watt University Riccarton, Edinburgh, EH14 4AS, UK E-mail: m.j.paterson@hw.ac.uk m.w.p.bebbington@hw.ac.uk http://www.theophotochem.eps.hw.ac.uk/Home.html , http://www.hw.ac.uk/schools/engineering-physical-sciences/staff-directory/mb.htm.
authors.forename: Lorna
authors.initials: L
authors.lastname: Kennedy
authors.affiliation: School of EPS - Institute of Chemical Sciences, Heriot-Watt University Riccarton, Edinburgh, EH14 4AS, UK E-mail: m.j.paterson@hw.ac.uk m.w.p.bebbington@hw.ac.uk http://www.theophotochem.eps.hw.ac.uk/Home.html , http://www.hw.ac.uk/schools/engineering-physical-sciences/staff-directory/mb.htm.
authors.forename: Justyna M
authors.initials: JM
authors.lastname: Żurek
authors.affiliation: School of EPS - Institute of Chemical Sciences, Heriot-Watt University Riccarton, Edinburgh, EH14 4AS, UK E-mail: m.j.paterson@hw.ac.uk m.w.p.bebbington@hw.ac.uk http://www.theophotochem.eps.hw.ac.uk/Home.html , http://www.hw.ac.uk/schools/engineering-physical-sciences/staff-directory/mb.htm.
authors.forename: Martin J
authors.initials: MJ
authors.lastname: Paterson
authors.affiliation: School of EPS - Institute of Chemical Sciences, Heriot-Watt University Riccarton, Edinburgh, EH14 4AS, UK E-mail: m.j.paterson@hw.ac.uk m.w.p.bebbington@hw.ac.uk http://www.theophotochem.eps.hw.ac.uk/Home.html , http://www.hw.ac.uk/schools/engineering-physical-sciences/staff-directory/mb.htm.
authors.forename: Magnus W P
authors.initials: MW
authors.lastname: Bebbington
keywords: Heterocyclic chemistry; Macrocycles; McMurry coupling; Photochemistry; Porphycenes; Redox chemistry