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Valente, Edward J.
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article
2,5-Dihydroxy-1,4-quinones appended with two phosphinyl groups: syntheses, structures, and redox properties
Abstract
<jats:title>Abstract</jats:title><jats:p>Low temperature reactions of 1,4-dichloro-2,5-dimethoxybenzene with two equivalents of lithium diisopropylamide (LDA) followed by quenches with chlorophosphines ClPR<jats:sub>2</jats:sub> (<jats:italic>R</jats:italic> = Ph or <jats:italic>i</jats:italic>Pr) yielded 1,4-bis(diphenylphosphino)-2,5-dichloro-3,6-dimethoxy-benzene (<jats:bold>1a</jats:bold>) and 1,4-bis(diisopropylphosphino)-2,5-dichloro-3,6-dimethoxy-benzene (<jats:bold>1b</jats:bold>). Reactions of <jats:bold>1a-b</jats:bold> with 30% hydrogen peroxide yielded 1,4-bis(diphenylphosphinyl)-2,5-dichloro-3,6-dimethoxybenzene (<jats:bold>2a</jats:bold>) and 1,4-bis(diisopropylphosphinyl)-2,5-dichloro-3,6-dimethoxybenzene (<jats:bold>2b</jats:bold>). Subjecting compounds <jats:bold>2a-b</jats:bold> to BBr<jats:sub>3</jats:sub>/CH<jats:sub>3</jats:sub>OH resulted in 2,5-bis(diphenylphosphinyl)-3,6-dichlorohydroquinone <jats:bold>3a</jats:bold> and 2,5-bis(diisopropylphosphinyl)-3,6-dichlorohydroquinone <jats:bold>3b</jats:bold>. Reactions of <jats:bold>3a-b</jats:bold> with K<jats:sub>2</jats:sub>S<jats:sub>2</jats:sub>O<jats:sub>8</jats:sub> under basic conditions followed by acidification allowed for isolation of 2,5-bis(diphenylphosphinyl)-3,6-dihydroxy-quinone (<jats:bold>4a</jats:bold>) and 2,5-bis(diisopropylphosphinyl)-3,6-dihydroxy-quinone (<jats:bold>4b</jats:bold>). Compounds <jats:bold>1a-b</jats:bold> – <jats:bold>4a-b</jats:bold> were fully characterized by spectroscopic methods (nuclear magnetic resonance [FT-NMR] spectroscopy, infrared [FT-IR] spectroscopy, and high resolution mass spectrometry [HRMS]); <jats:bold>3a-b</jats:bold> and <jats:bold>4a-b</jats:bold> were also investigated by cyclic voltammetry. Compounds <jats:bold>1a-b</jats:bold> , <jats:bold>2a</jats:bold> , and <jats:bold>4a-b</jats:bold> were also characterized by single-crystal X-ray diffraction methods.</jats:p>