Journal article

Publication year: 1978

Pages: 2630-2645

Journal: Chemische Berichte

Volume number: 111

Issue number: 7

ISSN: 0009-2940

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

Publisher: 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 Citation style: 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 Citation style: 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