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Communication

CF3-Bis-TEMPO-Vis: New Visible Light Active Bis-Benzimidazolequinone Alkoxyamine

1
School of Chemistry, National University of Ireland Galway, University Road, H91 TK33 Galway, Ireland
2
Department of Pharmacy, School of Life Sciences, Pharmacy and Chemistry, Kingston University, Penrhyn Road, Kingston upon Thames KT1 2EE, UK
*
Author to whom correspondence should be addressed.
Academic Editor: Nicholas E. Leadbeater
Molbank 2021, 2021(4), M1300; https://doi.org/10.3390/M1300
Received: 2 November 2021 / Revised: 18 November 2021 / Accepted: 23 November 2021 / Published: 26 November 2021
(This article belongs to the Collection Heterocycle Reactions)
Alkoxyamines of TEMPO usually dissociate thermally at >100 °C; however, room temperature homolysis, activated by visible light, occurs with benzimidazolequinone derivatives. 1,1’-Dimethyl-2,2’-bis{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-6-(trifluoromethyl)-1H,1’H-[5,5’-bibenzimidazole]-4,4’,7,7’-tetrone (CF3-Bis-TEMPO-Vis) is prepared in a 59% yield through NBS/H2SO4 oxidative demethylations of the dimethoxybenzimidazole-benzimidazolequinone precursor with aqueous work up. The alternative basic work up in air gave the epoxide derivative of CF3-Bis-TEMPO-Vis. Unlike the latter CF3-epoxide, both alkoxyamine residues are labile under green light (470–600 nm), and the rate of TEMPO release is three times slower than Bis-TEMPO-Vis. View Full-Text
Keywords: epoxide; homolysis; kinetics; nitroxide; quinones; radicals epoxide; homolysis; kinetics; nitroxide; quinones; radicals
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MDPI and ACS Style

Kielty, P.; Farràs, P.; Smith, D.A.; Aldabbagh, F. CF3-Bis-TEMPO-Vis: New Visible Light Active Bis-Benzimidazolequinone Alkoxyamine. Molbank 2021, 2021, M1300. https://doi.org/10.3390/M1300

AMA Style

Kielty P, Farràs P, Smith DA, Aldabbagh F. CF3-Bis-TEMPO-Vis: New Visible Light Active Bis-Benzimidazolequinone Alkoxyamine. Molbank. 2021; 2021(4):M1300. https://doi.org/10.3390/M1300

Chicago/Turabian Style

Kielty, Patrick, Pau Farràs, Dennis A. Smith, and Fawaz Aldabbagh. 2021. "CF3-Bis-TEMPO-Vis: New Visible Light Active Bis-Benzimidazolequinone Alkoxyamine" Molbank 2021, no. 4: M1300. https://doi.org/10.3390/M1300

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