Selective cross-acyloin condensation catalyzed by thiazolium salt. Formation of 1-hydroxy 2-one from formaldehyde and other aldehydes

T Matsumoto, M Ohishi, S Inoue

Index: Matsumoto, Toshihiko; Ohishi, Masafumi; Inoue, Shohei Journal of Organic Chemistry, 1985 , vol. 50, # 5 p. 603 - 606

Full Text: HTML

Citation Number: 63

Abstract

The condensation of formaldehyde with another aldehyde catalyzed by 3- ethylbenzothiazolium bromide in the presence of triethylamine gives selectively 1-hydroxy 2- ones. This selective cross-acyloin condensation indicates an inverse selectivity in the reactions of the conjugate base of thiazolium salt 17 and of the carbanion bound to thiazolium ring 19 toward aldehyde.

Related Articles:

Meerwein-Ponndorf-Verley-type reduction of dicarbonyl compounds to hydroxy carbonyl compounds and. alpha.,. beta.-unsaturated carbonyl compounds to allylic …

[Nakano, Tatsuya; Umano, Shigetoshi; Kino, Yoshio; Ishii, Yasutaka; Ogawa, Masaya Journal of Organic Chemistry, 1988 , vol. 53, # 16 p. 3752 - 3757]

Oxidation of ketone by palladium (II). α-Hydroxyketone synthesis catalyzed by a bimetallic palladium (II) complex

[El-Qisairi, Arab K; Qaseer, Hanan A Journal of Organometallic Chemistry, 2002 , vol. 659, # 1-2 p. 50 - 55]

Multistage screening reveals chameleon ligands of the human farnesyl pyrophosphate synthase: implications to drug discovery for neurodegenerative diseases

[Waszkuc, Wieslaw; Janecki, Tomasz; Bodalski, Ryszard Synthesis, 1984 , # 12 p. 1025 - 1027]

Oxidation of 3-butene-1, 2-diol by alcohol dehydrogenase

[Kemper, Raymond A.; Elfarra, Adnan A. Chemical Research in Toxicology, 1996 , vol. 9, # 7 p. 1127 - 1134]

Oxidation of 3-butene-1, 2-diol by alcohol dehydrogenase

[Kemper, Raymond A.; Elfarra, Adnan A. Chemical Research in Toxicology, 1996 , vol. 9, # 7 p. 1127 - 1134]

More Articles...