Fleming-Tamao oxidation

The Fleming-Tamao oxidation , also known as the Tamao oxidation or Tamao-Fleming oxidation, is a name reaction in organic chemistry . It was discovered in 1983 by the Japanese chemist Kohei Tamao (* 1942) and the British chemist Ian Fleming (* 1935). The reaction allows the synthesis of primary alcohols or secondary alcohols .

Overview reaction

The oxidation reaction results in a conversion of an organic silicon compound to an alcohol. This requires hydrogen peroxide and potassium fluoride .

R is an organic radical e.g. B. an alkyl radical .

Reaction mechanism

The following reaction mechanism comes from the book "Comprehensive Organic Name Reactions and Reagents" and is only one possible reaction mechanism:

The organometallic compound 1 reacts with the fluoride , splitting off an isopropoxide to form 2 . The organometallic 2 combines with a dioxide anide , with the elimination of another isopropoxide, to form 3 . The split-off isopropoxide attacks the silicon of 3 . By shifting a hydroxyl group, the organic radical RCH _{2 is} split off, thus producing alcohol 4 .

The dioxide anide, which is required in the second step, can be produced by the reaction of isopropoxide with hydrogen peroxide:

Individual evidence

↑ László Kürti , Barbara Czakó: Strategic Applications of named reactions in organic synthesis. Background and detailed mechanisms. 250 named reactions. Elsevier - Academic Press, Amsterdam et al. 2005, ISBN 0-12-369483-3 , p. 174.
^ Zerong Wang: Comprehensive Organic Name Reactions and Reagents. Volume 1. John Wiley & Sons, Hoboken NJ 2009, ISBN 978-0-471-70450-8 , p. 1103.
^ ^A ^b Zerong Wang: Comprehensive Organic Name Reactions and Reagents. Volume 1. John Wiley & Sons, Hoboken NJ 2009, ISBN 978-0-471-70450-8 , p. 1104.
↑ László Kürti, Barbara Czakó: Strategic Applications of named reactions in organic synthesis. Background and detailed mechanisms. 250 named reactions. Elsevier - Academic Press, Amsterdam et al. 2005, ISBN 0-12-369483-3 , pp. 174, 175.
↑ Kohei Tamao, Neyoshi Ishida, Tatsu Tanaka, Makoto Kumada: Silafunctional compounds in organic synthesis. Part 20. Hydrogen peroxide oxidation of the silicon-carbon bond in organoalkoxysilanes . In: Organometallics . tape 2 , no. 11 , 1983, pp. 1694-1696 , doi : 10.1021 / om50005a041 .

[Kuerti_und_Czako390-1] László Kürti , Barbara Czakó: Strategic Applications of named reactions in organic synthesis. Background and detailed mechanisms. 250 named reactions. Elsevier - Academic Press, Amsterdam et al. 2005, ISBN 0-12-369483-3 , p. 174.

[Wang_1103-2] Zerong Wang: Comprehensive Organic Name Reactions and Reagents. Volume 1. John Wiley & Sons, Hoboken NJ 2009, ISBN 978-0-471-70450-8 , p. 1103.

[Wang_1104-3] A ^b Zerong Wang: Comprehensive Organic Name Reactions and Reagents. Volume 1. John Wiley & Sons, Hoboken NJ 2009, ISBN 978-0-471-70450-8 , p. 1104.

[Kuerti_und_Czako-4] László Kürti, Barbara Czakó: Strategic Applications of named reactions in organic synthesis. Background and detailed mechanisms. 250 named reactions. Elsevier - Academic Press, Amsterdam et al. 2005, ISBN 0-12-369483-3 , pp. 174, 175.

[Tamao_and_co.-5] Kohei Tamao, Neyoshi Ishida, Tatsu Tanaka, Makoto Kumada: Silafunctional compounds in organic synthesis. Part 20. Hydrogen peroxide oxidation of the silicon-carbon bond in organoalkoxysilanes . In: Organometallics . tape 2 , no. 11 , 1983, pp. 1694-1696 , doi : 10.1021 / om50005a041 .