Big Chemical Encyclopedia

Chemical substances, components, reactions, process design ...

Articles Figures Tables About

Glyoxal benzilic acid rearrangement

O Meara, D., Richards, G. N. Mechanism of saccharinic acid formation. IV. Influence of cations in the benzilic acid rearrangement of glyoxal. J. Chem. Soc. 1960, 1944-1945. [Pg.548]

The prototype reaction is the conversion of glyoxal into glycolic acid (equation 2), and here the benzilic acid rearrangement mechanism coincides with that for an intramolecular Cannizzaro reaction. The reaction is observed with other purely aliphatic a-diketones such as f-butyl 2,3-dioxobutyrate and cyclohexane-1,2-dione (equations 3 and 4), but the scope is limited in the aliphatic series by competing (c.g. aldol) reactions. Suitably constructed heterocyclic systems also rearrange, and the conversion of alloxan (3) into alloxanic acid (4) was among the first of the benzilic acid rearrangements to be discovered (equation 5). ... [Pg.822]

The Benzilic Acid Rearrangement When benzil is treated with sodium hydroxide, benzilic acid is fornied and the reaction appears to proceed by the intramolecular addition of a group with an electron pair to the carbonyl carbon atom. A mechanism which seems quite plausible for the reaction is the following.50 It is identical mechanistically with the glyoxal-glyoolic acid rearrangement (p. 107). [Pg.199]

The released end-group forms an a-dicarbonyl structure which rearranges by an intramolecular, Cannizzaro type of reaction to yield saccharinates. Intramolecular reactions of the Cannizzaro type can occur not only with dialdehydes but also with a-ketoaldehydes and a-diketones ( benzilic acid rearrangement ) they can be exemplified by the base-catalyzed rearrangement of phenylglyoxal (VIII) [or of (2,4,6-trimethylphenyl)-glyoxal ] to the salt of mandelic acid (IX) (or of 2,4,6-trimethylmandelic acid). [Pg.297]

Novelli, A., Barrio, J. R. Carbon-14 tracer studies in the benzilic acid type rearrangement of 1-phenyl-and 1-(4-methoxyphenyl)-2-(3-pyridyl) glyoxal. Tetrahedron Lett. 1969, 3671-3672. [Pg.549]


See other pages where Glyoxal benzilic acid rearrangement is mentioned: [Pg.98]    [Pg.98]    [Pg.96]    [Pg.54]    [Pg.54]   
See also in sourсe #XX -- [ Pg.3 ]

See also in sourсe #XX -- [ Pg.831 ]

See also in sourсe #XX -- [ Pg.3 ]




SEARCH



Benzil

Benzil rearrangement

Benzil-benzilic acid

Benzil-benzilic acid rearrangement

Benzile

Benzilic acid

Benzilic rearrangement

Benzils

Benzils rearrangement

Glyoxalate

Glyoxalic

Glyoxalic acid

Glyoxals

Rearrangements benzilic acid

© 2024 chempedia.info