Acyloxy group

Acyloxy radical ( blue ) as part of the structural formula of acetylsalicylic acid. In the example, the acyloxy group is an acetyloxy group that is derived from acetic acid.

In chemistry , acyloxy group , acyloxy , azyloxy or alkanoyloxy is a functional group with the general structure R- (C = O) O-, where R is an organyl radical ( alkyl or aryl, etc.) or a hydrogen atom can. The acyloxy group is formally derived from carboxylic acids in which the hydrogen atom of the OH group has been substituted by a radical .

The introduction of an acyloxy group into a molecule is called acyloxylation. To introduce an acyloxy group into an organic molecule, the implementation of percarboxylic acid esters ( Kharasch-Sosnovsky reaction ) or the use of metal salts (Pb, Hg, Tl, Pd etc.) of the carboxylic acids as starting material are suitable. In the Kolbe synthesis ( electrolysis of the sodium or potassium salts of carboxylic acids in aqueous solution), acyloxy radicals are formed in the first step through anodic oxidation of the acyloxy anions ( carboxylate ions ). It is assumed that N -nitroso derivatives of carboxylic acid anilides rearrange to form N- acyloxy compounds, which decompose to form phenyl radicals.

The acyloxy group with the indefinite radical R is the generic term for the acetyloxy group (“AcO”), the benzoyloxy group and similar radicals. The acyloxy group should not match the acyl group - e.g. B. Acetyl group ("Ac") or benzoyl group - be confused.

Individual evidence

1. ↑ ^{a b} Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 1: A-Cl. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1979, ISBN 3-440-04511-0 , p. 62.
2. ^ Siegfried Hauptmann : Organic Chemistry , 2nd revised edition, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, pp. 204–205, ISBN 3-342-00280-8 .
3. ↑ Michael B. Smith: March's advanced organic chemistry , John Wiley & Sons, 7th Edition, 2013, pp. 795-796, ISBN 978-0-470-46259-1 .