Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Mozingo reduction

From Wikipedia, the free encyclopedia
Mozingo reduction
Named afterRalph Mozingo
Reaction typeOrganic redox reaction

TheMozingo reduction, also known asMozingo reaction orthioketal reduction, is achemical reaction capable of fullyreducing aketone oraldehyde to the correspondingalkane via adithioacetal.[1][2] The reaction scheme is as follows:[3]

The ketone or aldehyde is activated by conversion to cyclicdithioacetal by reaction with adithiol (nucleophilic substitution) in presence of a H+ donating acid. The cyclic dithioacetal structure is thenhydrogenolyzed usingRaney nickel. Raney nickel is converted irreversibly tonickel sulfide. This method is milder than either theClemmensen orWolff-Kishner reductions, which employ strongly acidic or basic conditions, respectively, that might interfere with otherfunctional groups.[4]

History

[edit]

The reaction is named after Ralph Mozingo, who reported the cleavage ofthioethers with Raney nickel in 1942.[5] However the modern iteration of the reaction, involving the cyclic dithioacetal, was developed byMelville Wolfrom.[6]

References

[edit]
  1. ^Francis A. Carey; Richard J. Sundberg (2007).Advanced Organic Chemistry: Reactions and synthesis.Springer. pp. 452–454.ISBN 9780387683508.
  2. ^Mosettig, Erich; Mozingo, Ralph (15 March 2011). "The Rosenmund Reduction of Acid Chlorides to Aldehydes".Organic Reactions:362–377.doi:10.1002/0471264180.or004.07.ISBN 978-0471264187.
  3. ^Jonathan Clayden; Nick Greeves; Stuart Warren (2012).Organic Chemistry (2 ed.).Oxford University Press.ISBN 9780199270293.
  4. ^Mitchell, Reginald; Lai, Yee-Hing (1980). "The neutral deoxygenation (reduction) of aryl carbonyl compounds with raney-nickel. an alternative to the clemmenson, wolf-kishner or mozingo (thioketal) reductions".Tetrahedron Letters.21 (27). Elsevier:2637–2638.doi:10.1016/S0040-4039(00)92825-9.
  5. ^du Vigneaud, Vincent; Melville, Donald B.; Folkers, Karl; Wolf, Donald E.; Mozingo, Ralph; Keresztesy, John C.; Harris, Stanton A. (December 1942)."The Structure of Biotin: A Study of Desthiobiotin".Journal of Biological Chemistry.146 (2):475–485.doi:10.1016/S0021-9258(18)44968-X.
  6. ^Wolfrom, M. L.; Karabinos, J. V. (June 1944). "Carbonyl Reduction by Thioacetal Hydrogenolysis".Journal of the American Chemical Society.66 (6):909–911.doi:10.1021/ja01234a021.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Mozingo_reduction&oldid=1074667414"
Categories:
[8]ページ先頭
©2009-2025 Movatter.jp