Mozingo reduction
Mozingo reduction | |
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Named after | Ralph Mozingo |
Reaction type | Organic redox reaction |
The Mozingo reduction, also known as Mozingo reaction or thioketal reduction, is a
The ketone or aldehyde is activated by conversion to cyclic
dithioacetal by reaction with a dithiol (nucleophilic substitution) in presence of a H+ donating acid. The cyclic dithioacetal structure is then hydrogenolyzed using Raney nickel. Raney nickel is converted irreversibly to nickel sulfide. This method is milder than either the Clemmensen or Wolff-Kishner reductions, which employ strongly acidic or basic conditions, respectively, that might interfere with other functional groups.[4]
History
The reaction is named after Ralph Mozingo, who reported the cleavage of
thioethers with Raney nickel in 1942.[5] However the modern iteration of the reaction, involving the cyclic dithioacetal, was developed by Melville Wolfrom.[6]
References
- ISBN 9780387683508.
- ISBN 978-0471264187.
- ISBN 9780199270293.
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