title: Facile and High-Yielding Synthesis of TAM Biradicals and Monofunctional TAM Radicals.
abstract: Facile and high-yielding procedures for synthesis of monocarboxylic acid derivatives of triarylmethyl radicals (TAMs) were developed. Reaction of methyl thioglycolate with tris(2,3,5,6-tetrathiaaryl)methyl cation smoothly afforded the monosubstituted TAM derivative, which was hydrolyzed to a monocarboxylic acid, with the TAM moiety attached to thioglycolic acid via the sulfur atom. Alternatively, the diamagnetic tricarboxylic acid precursor of Finland trityl was transformed to a trimethyl ester and partially hydrolyzed under controlled conditions. The diester product was isolated and the remaining fractions were converted back to the trimethyl ester for production of more diester. The first representatives of TAM biradicals with different TAM cores and interspin distances were obtained by reaction of these new TAM monocaboxylic acids with N,N'-dimethylethylenediamine.
authors.affiliation: Novosibirsk Institute of Organic Chemistry, 9 Academician Lavrentiev Ave., Novosibirsk 630090, Russia, ; Department of Natural Sciences, Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090, Russia.
authors.forename: Dmitry V
authors.initials: DV
authors.lastname: Trukhin
authors.affiliation: Novosibirsk Institute of Organic Chemistry, 9 Academician Lavrentiev Ave., Novosibirsk 630090, Russia, ; Department of Natural Sciences, Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090, Russia.
authors.forename: Olga Yu
authors.initials: OY
authors.lastname: Rogozhnikova
authors.affiliation: Novosibirsk Institute of Organic Chemistry, 9 Academician Lavrentiev Ave., Novosibirsk 630090, Russia.
authors.forename: Tatiana I
authors.initials: TI
authors.lastname: Troitskaya
authors.affiliation: Novosibirsk Institute of Organic Chemistry, 9 Academician Lavrentiev Ave., Novosibirsk 630090, Russia.
authors.forename: Vladimir G
authors.initials: VG
authors.lastname: Vasiliev
authors.affiliation: Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, AL 35487-0336, USA.
authors.forename: Michael K
authors.initials: MK
authors.lastname: Bowman
authors.affiliation: Novosibirsk Institute of Organic Chemistry, 9 Academician Lavrentiev Ave., Novosibirsk 630090, Russia, ; Department of Natural Sciences, Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090, Russia.
authors.forename: Victor M
authors.initials: VM
authors.lastname: Tormyshev
keywords: TAM derivatives; biradicals; free radicals; persistent triarylmethyls; spin labels