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Facile and High-Yielding Synthesis of TAM Biradicals and Monofunctional TAM Radicals Full article

Journal Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096
Output data Year: 2016, Volume: 27, Number: 6, Pages: 893-899 Pages count : 7 DOI: 10.1055/s-0035-1561299
Tags free radicals; persistent triarylmethyls; TAM derivatives; spin labels; biradicals
Authors Trukhin Dmitry V. 1,2 , Rogozhnikova Olga Yu. 1,2 , Troitskaya Tatiana I. 1 , Vasiliev Vladimir G. 1 , Bowman Michael K. 3 , Tormyshev Victor M. 1,2
Affiliations
1 (Данные Web of science) Novosibirsk Organ Chem Inst, 9 Academician Lavrentiev Ave, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, 2 Pirogova St, Novosibirsk 630090, Russia
3 (Данные Web of science) Univ Alabama, Dept Chem, Box 870336, Tuscaloosa, AL 35487 USA

Abstract: Facile and high-yielding procedures for the synthesis of monocarboxylic acid derivatives of triarylmethyl radicals (TAM) 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 into 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.
Cite: Trukhin D.V. , Rogozhnikova O.Y. , Troitskaya T.I. , Vasiliev V.G. , Bowman M.K. , Tormyshev V.M.
Facile and High-Yielding Synthesis of TAM Biradicals and Monofunctional TAM Radicals
Synlett. 2016. V.27. N6. P.893-899. DOI: 10.1055/s-0035-1561299 WOS Scopus РИНЦ
Files: Full text from publisher
Dates:
Published online: Dec 23, 2015
Identifiers:
Web of science WOS:000372984600018
Scopus 2-s2.0-84962527105
Elibrary 26984196
OpenAlex W2269425272
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