Mutual Influence of (Dimethylhydrazono)methyl Groups and ?-Hydroxy Ketone Moieties in Hetaryl Analogues of Unsymmetric Benzoins

Autor:	Sergey P. Ivonin, Andrey A. Anishchenko, Andrey V. Lapandin, V. G. Shtamburg
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Phenylglyoxal Ketone Nitrile Organic Chemistry Aldehyde Residue (chemistry) Electrophilic substitution chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry Isomerization Methyl group
Zdroj:	European Journal of Organic Chemistry. 2004:4688-4693
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200400293
Popis:	Reactions between phenylglyoxal hydrate and the N,N-dimethylhydrazones of furfural and pyrrole-2-carbaldehyde run regioselectively at the 5-position of the heterocycle. The resulting hetaryl analogues of α-benzoins quantitatively isomerize to β-compounds, the (dimethylhydrazono)methyl group activating the hetaryl residue and thus affording faster isomerization than in their unfunctionalized counterparts. The (dimethylhydrazono)methyl group is easily convertible into the aldehyde or nitrile group and can also be involved in rehydrazonation. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f1948443092d0f1a90902ad0d2212eb2 https://doi.org/10.1002/ejoc.200400293 Zobrazit plný text záznamu Plný text