Mozingova redukce

Mozingova redukce, známá také jako Mozingova reakce nebo thioketalová redukce, je chemická reakce schopná plně redukovat keton nebo aldehyd na odpovídající alkan prostřednictvím dithioacetalu.[1][2] Schéma reakce je následující:[3]

Keton nebo aldehyd se aktivuje konverzí na cyklický dithioacetal reakcí s dithiolem (nukleofilní substituce) v přítomnosti H+ donující kyseliny. Cyklická dithioacetalová struktura se poté hydrogenolyzuje pomocí Raneyova niklu. Raneyův nikl se nevratně přemění na sulfid nikelnatý. Tato metoda je mírnější než Clemmensenova nebo Wolffova–Kižněrova redukce, které používají silně kyselé, resp. zásadité podmínky, které by mohly interferovat s jinými funkčními skupinami.[4]

Historie

Reakce je pojmenována po Ralphu Mozingovi, který v roce 1942 popsal štěpení thioetherů pomocí Raneyova niklu.[5] Moderní iteraci reakce, zahrnující cyklický dithioacetal, však vyvinul Melville Wolfrom.[6]

Reference

V tomto článku byl použit překlad textu z článku Mozingo reduction na anglické Wikipedii.

  1. CAREY, Francis A.; SUNDBERG, Richard J. Advanced Organic Chemistry: Reactions and synthesis. [s.l.]: Springer, 2007. ISBN 9780387683508. S. 452–454. 
  2. MOSETTIG, Erich; MOZINGO, Ralph. The Rosenmund Reduction of Acid Chlorides to Aldehydes. [s.l.]: [s.n.], 2011. ISBN 978-0471264187. DOI 10.1002/0471264180.or004.07. S. 362–377. 
  3. CLAYDEN, Jonathan; GREEVES, Nick; WARREN, Stuart. Organic Chemistry. 2.. vyd. [s.l.]: Oxford University Press, 2012. Dostupné online. ISBN 9780199270293. 
  4. REGINALD, Mitchell; LAI, Lai. The neutral deoxygenation (reduction) of aryl carbonyl compounds with raney-nickel. an alternative to the clemmenson, wolf-kishner or mozingo (thioketal) reductions. S. 2637–2638. Tetrahedron Letters [online]. Elsevier [cit. 2022-09-21]. S. 2637–2638. DOI 10.1016/S0040-4039(00)92825-9. 
  5. DU VIGNEAUD, Vincent; MELVILLE, Donald B.; FOLKERS, Karl, Donald E. Wolf, Ralph Mozingo, John C. Keresztesy, Stanton A. Harris. The Structure of Biotin: A Study of Desthiobiotin. S. 475–485. Journal of Biological Chemistry [online]. [cit. 2022-09-21]. Roč. 146, čís. 2, s. 475–485. DOI 10.1016/S0021-9258(18)44968-X. 
  6. WOLFROM, M. L.; KARABINOS, J. V. Carbonyl Reduction by Thioacetal Hydrogenolysis. S. 909–911. Journal of the American Chemical Society [online]. [cit. 2022-09-21]. Roč. 66, čís. 6, s. 909–911. DOI 10.1021/ja01234a021. 

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