title: Functional group transformations in derivatives of 6-oxoverdazyl.
abstract: Transformations of functional groups, such as OCH2Ph, OCOPh, NO2 and I, in 1,3,5-triphenyl-6-oxoverdazyls 1a-1e were investigated in order to expand the range of synthetic tools for incorporation of the verdazyl system into more complex molecular architectures and to increase spin delocalization. Thus, Pd-catalyzed debenzylation of the OCH2Ph group or basic hydrolysis of the OCOPh group gave the phenol functionality, which was acylated, but could not be alkylated. Orthogonal deprotection of diphenol functionality was also demonstrated in radical 1c. Pt-catalyzed reduction of the NO2 group led to the aniline derivative, which was acylated. Attempted C-C coupling reactions to iodophenyl derivatives 1e and 5e were unsuccessful. Selected verdazyl radicals were characterized by EPR and electronic absorption spectroscopy, and results were analyzed with the aid of DFT computational methods.
authors.affiliation: Faculty of Chemistry, University of Łódź, Łódź, Poland.
authors.forename: Marcin
authors.initials: M
authors.lastname: Jasiński
authors.forename: Jason S
authors.initials: JS
authors.lastname: Gerding
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Jankowiak
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Gębicki
authors.forename: Jarosław
authors.initials: J
authors.lastname: Romański
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Jastrzębska
authors.forename: Ajan
authors.initials: A
authors.lastname: Sivaramamoorthy
authors.forename: Kristein
authors.initials: K
authors.lastname: Mason
authors.forename: Donavan H
authors.initials: DH
authors.lastname: Evans
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Celeda
authors.forename: Piotr
authors.initials: P
authors.lastname: Kaszyński
mesh_terms: D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D005609:Free Radicals; D006571:Heterocyclic Compounds