title: Synthesis of Hydrodipyrrins Tailored for Reactivity at the 1- and 9-Positions.
abstract: A collection of 33 hydrodipyrrins (9 targets, 21 intermediates, and 3 byproducts) has been prepared. The hydrodipyrrins (dihydrodipyrrins, tetrahydrodipyrrins, and hexahydrodipyrrins) contain a pyrrole ring and a geminal-dimethyl substituted 1-pyrroline (or pyrrolidine) ring. The alpha-substituents on the pyrrole ring (H, Br, CHO) and pyrroline ring (H, CH(3), CH(OR)(2), OMe, SMe) provide different reactivity combinations (Nu(-), E(+)) and 0, 1, or 2 carbon atoms (which can give rise to the bridging meso-carbons in hydroporphyrins). Straightforward access to various hydrodipyrrins should facilitate development of syntheses of diverse hydroporphyrins.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Han-Je
authors.initials: HJ
authors.lastname: Kim
authors.forename: Dilek Kiper
authors.initials: DK
authors.lastname: Dogutan
authors.forename: Marcin
authors.initials: M
authors.lastname: Ptaszek
authors.forename: Jonathan S
authors.initials: JS
authors.lastname: Lindsey