Abstract:
Reduction of aldehyde group in 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde leads to methoxymethyl (NaBH4, MeOH) or methyl (Zn, MeOH) analogues, which were further oxidized into the corresponding o-benzoquinones. Their photostability in benzene increases substantially on replacement of the 6-positioned Me substituent with the CH2OMe group.
Document Type:
Article
Language: English
Citation:
M. V. Arsenyev, E. V. Baranov, M. P. Shurygina, S. A. Chesnokov, G. A. Abakumov, “New sterically-hindered catechols/o-benzoquinones. Reduction of 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde”, Mendeleev Commun., 26:6 (2016), 552–554
Linking options:
https://www.mathnet.ru/eng/mendc2278
https://www.mathnet.ru/eng/mendc/v26/i6/p552
This publication is cited in the following 18 articles:
M. P. Shurygina, M. V. Arsenyev, E. V. Baranov, M. A. Baten'kin, M. Yu. Zakharina, E. R. Zhiganshina, A. N. Konev, S. A. Chesnokov, “Synthesis and properties of a new photoinitiator of polymerization by visible irradiation based on 3,5-di-tert-butyl-o-benzoquinone”, Russ Chem Bull, 73:11 (2024), 3429
A. Z. Kamaletdinov, A. V. Smolobochkin, A. S. Gazizov, E. A. Chugunova, E. R. Zhiganshina, V. V. Syakaev, A. B. Dobrynin, A. R. Burilov, M. A. Pudovik, “Synthesis of A New Imidazocoumarin by Reaction of 1-Methyl-3-phenyl-1,3-dihydro-2H-imidazol-2-one with 4,6-Di-tert-butyl-3-(methoxymethyl)benzene-1,2-diol”, Russ J Gen Chem, 93:S2 (2023), S510
N. Yu. Shushunova, D. V. Khramova, T. A. Kovylina, M. V. Arsenyev, E. R. Zhiganshina, S. A. Chesnokov, “Pyrazole-Containing o-Benzoquinones: Synthesis and Inhibitory Activity in Free-Radical Polymerization”, Russ J Gen Chem, 93:S3 (2023), S639
A. E. Tarakanova, N. D. Anisimova, D. A. Martynova, N. M. Khamaletdinova, E. V. Baranov, M. V. Arsenyev, S. A. Chesnokov, “Alkylation of Phenols with 4,6-Di-tert-butyl-3-methoxymethylcatechol. Antiradical Activity of Sterically Hindered Catecholphenols”, Russ J Gen Chem, 93:S3 (2023), S629
Yaroslav V. Bolt, Maxim A. Dubinnyi, Veronika V. Litvinenko, Alexey A. Kotlobay, Olga A. Belozerova, Renata I. Zagitova, Vladimir I. Shmygarev, Oleg N. Yatskin, Elena B. Guglya, Vadim S. Kublitski, Mikhail S. Baranov, Ilia V. Yampolsky, Zinaida M. Kaskova, Aleksandra S. Tsarkova, “Total Synthesis of Racemic Thieno[3,2-f]thiochromene Tricarboxylate, a Luciferin from Marine Polychaeta Odontosyllis undecimdonta”, Org. Lett., 25:26 (2023), 4892
E. R. Zhiganshina, V. S. Lysenkov, T. I. Lopatina, M. V. Arsenyev, S. A. Chesnokov, “(Met)acrylate-Containing Sterically Hindered o-Benzoquinones for free Radical Polymerization”, High Energy Chem, 56:3 (2022), 163
Ivan V. Smolyaninov, Daria A. Burmistrova, Maxim V. Arsenyev, Maria A. Polovinkina, Nadezhda P. Pomortseva, Georgy K. Fukin, Andrey I. Poddel'sky, Nadezhda T. Berberova, “Synthesis and Antioxidant Activity of New Catechol Thioethers with the Methylene Linker”, Molecules, 27:10 (2022), 3169
M. A. Zherebtsov, E. R. Zhiganshina, N. A. Lenshina, R. S. Kovylin, E. V. Baranov, N. Yu. Shushunova, M. P. Shurygina, M. V. Arsenyev, S. A. Chesnokov, V. K. Cherkasov, “Synthesis and photoinitiating ability of substituted 4,5-di-tert-alkyl-o-benzoquinones in radical polymerization”, Russ Chem Bull, 70:4 (2021), 780
S. K. Polyakova, T. V. Balashova, R. V. Rumyantcev, M. V. Arsenyev, G. K. Fukin, S. A. Chesnokov, “Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols”, Mendeleev Commun., 31:2 (2021), 262–264
M. A. Zherebtsov, M. V. Arsenyev, E. V. Baranov, S. A. Chesnokov, V. K. Cherkasov, “Synthesis and structure of sterically hindered o-benzoquinone carboxylic acid”, Mendeleev Commun., 31:2 (2021), 268–270
Margarita P. Shurygina, Maria Yu. Zakharina, Maxim A. Baten'kin, Alexey N. Konev, Andrey S. Shavyrin, Egor A. Chelnokov, Nataliya Yu. Shushunova, Maxim V. Arsenyev, Sergey A. Chesnokov, Gleb A. Abakumov, “A blue to red light sensitive photoinitiating systems based on 3,5-di-tert-butyl-o-benzoquinone derivatives for free radical polymerization”, European Polymer Journal, 127 (2020), 109573
S. Yu. Bukhvalova, E. R. Zhiganshina, T. V. Astaf'eva, M. V. Arsenyev, E. V. Baranov, S. A. Chesnokov, A. I. Poddel'sky, “New Sterically Hindered Bis-o-Benzoquinones with Electron-Donor Bridging Groups and Related Binuclear Triphenylantimony(V) Catecholate Complexes”, Russ J Coord Chem, 46:12 (2020), 817
M. A. Zherebtsov, M. V. Arsenyev, S. A. Chesnokov, V. K. Cherkasov, “Synthesis of 1-Substituted
5,5,8,8-Tetramethyl5,6,7,8-tetrahydronaphthalene-2,3-diols and
5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2,3-dione”, Russ J Org Chem, 56:3 (2020), 534
E. R. Zhiganshina, M. V. Arsenyev, A. S. Shavyrin, E. V. Baranov, S. A. Chesnokov, “Trans-etherification of catechol-type benzylic ether with diols as a route to new sterically hindered bis-catechols”, Mendeleev Commun., 29:1 (2019), 91–93
Andrey I. Poddel'sky, Tatyana V. Astaf'eva, Ivan V. Smolyaninov, Maxim A. Arsenyev, Georgy K. Fukin, Nadezhda T. Berberova, Vladimir K. Cherkasov, Gleb A. Abakumov, “Triphenylantimony(V) 6-alkoxymethyl-3,5-di-tert-butylcatecholates. Structure and redox-properties”, Journal of Organometallic Chemistry, 873 (2018), 57
M. V. Arsenyev, T. V. Astaf'eva, E. V. Baranov, A. I. Poddel'sky, S. A. Chesnokov, “New sterically hindered bis-catechol, bis-o-quinone and its bis-triphenylantimony(v) bis-catecholate. 3,5-Di-tert-butyl-6-methoxymethylcatechol as alkylating agent”, Mendeleev Commun., 28:1 (2018), 76–78
A. I. Poddel'sky, M. V. Arsen'ev, L. S. Okhlopkova, I. V. Smolyaninov, G. K. Fukin, “New catecholate complexes of triphenylantimony(V) based on 6-iminomethyl-3,5-di-tert-butylpyrocatechols N-functionalized by the aniline or phenol group”, Russ J Coord Chem, 43:12 (2017), 843
Andrey I. Poddel'sky, Maxim V. Arsenyev, Tatyana V. Astaf'eva, Sergey A. Chesnokov, Georgy K. Fukin, Gleb A. Abakumov, “New sterically-hindered 6th-substituted 3,5-di- tert -butylcatechols/ o -quinones with additional functional groups and their triphenylantimony(V) catecholates”, Journal of Organometallic Chemistry, 835 (2017), 17
Contact us: