ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Vinylogous Acyl Compounds. XX. Reactivity and Toxicity of Aryl-substituted β-Chlorovinyl Ketones, β-Chlorovinyl Aldehydes, and β-Chlorovinyl Methyleniminium SaltsBased on kinetic measurements, the nucleophilic replaceability of the chlorine in aromatic β-chlorovinyl ketones ArCO-CH = CH-Cl (1), isomeric β-chlorovinyl aldehydes OCH—CH=C(Cl)Ar(2), and corresponding β-chlorovinyl methyleniminium salts Me2N⊕;=CH—CH=C(Cl)Ar X⊖ (3) is compared and related to toxicological findings. The chemical reactivity of these important synthetic building blocks increases in the order 2〈1〈3, the acute toxicity (24 h LD50 i. p. in the mouse) shows the graduation 2〈3〈1. Compounds of type 1 prove to be relatively toxic (LD50 24-42 mg/kg) and display a marked necrotic action after percutaneous absorption, whereas the aldehydes 2 have not only a minor acute toxicity (LD50 158-298 mg/kg) but also a somewhat less marked skin damaging activity. In addition, the LD50 values of selected β-chlorovinyl carbonyl compounds are compared with those of corresponding halogen-free compounds as well as of vinylogous carbonamidium salts ArCO—CH=CH—N⊕R3X⊖. The latter, which can be used as synthetic equivalents of 1, differ in both the reduced acute toxicity and missing skin damaging properties.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19833250108
