Journalartikel

Jahr der Veröffentlichung: 1978

Seiten: 2630-2645

Zeitschrift: Chemische Berichte

Bandnummer: 111

Heftnummer: 7

ISSN: 0009-2940

DOI Link: https://doi.org/10.1002/cber.19781110718

Verlag: VCH-Verl.-Ges.

Abstract: 
Metalation of carcinogenic nitrosamines with K tert-butoxide/butyllithium/diisopropylamine (KDA) takes place more rapidly than with Li diisopropylamide (LDA) and leads to the more reactive K derivatives. The use of K tert-butoxide alone for C.sbd.C-bond formation between nitrosamines and carbonyl compounds in situ is feasible only with non-enolizable aromatic aldehydes and diarylketones; the addition under these conditions is reversible, the position of the equilibrium depends strongly upon steric factors. .alpha.-Stannylated nitrosamines add thermally to benzaldehydes and cinnamaldehyde to give stannylethers of the alcohols which are readily cleaved with aqueous acid. The poor yields of acylated nitrosamines obtained from the lithio derivatives with carboxylic acid esters, -chlorides, or -anhydrides can be greatly improved by employing acyl cyanides.

Harvard-Zitierstil: RENGER, B., HUGEL, H., WYKYPIEL, W. and SEEBACH, D. (1978) 3 NEW MODIFICATIONS OF C-C-BOND FORMATION WITH NITROSAMINES (GENERATION AND PREPARATION AS WELL AS REACTIONS OF POTASSIUM AND TIN DERIVATIVES - ACYLATIONS WITH ALPHA-KETONITRILES), Chemische Berichte, 111(7), pp. 2630-2645. https://doi.org/10.1002/cber.19781110718

APA-Zitierstil: RENGER, B., HUGEL, H., WYKYPIEL, W., & SEEBACH, D. (1978). 3 NEW MODIFICATIONS OF C-C-BOND FORMATION WITH NITROSAMINES (GENERATION AND PREPARATION AS WELL AS REACTIONS OF POTASSIUM AND TIN DERIVATIVES - ACYLATIONS WITH ALPHA-KETONITRILES). Chemische Berichte. 111(7), 2630-2645. https://doi.org/10.1002/cber.19781110718