Synthesis of 2-Substituted Cyclobutanones as γ-Irradiation Marker Products ofLipid-Containing Foods. -The alkylation of anions derived from imine (II) with the corresponding alkyl bromides followed by hydrolyzation of the resulting alkylated imines provides a short and efficient access to the target compounds. An important demand on the route to alkenyl and alkadienyl cyclobutanones (VIII) and (XII) is the stereochemical purity of these products, which is realized by an previously reported partial reduction of alkynols (V) and (IX). -(VERNIEST, G.; BOTERBERG, S.; COLPAERT, J.; VAN THIENEN, T.; STEVENS, C. V.; DE KIMPE*, N.; Synlett

Pyrrole derivativesPyrrole derivatives R 0120New Ring Expansion of Cyclobutanones: Synthesis of Pyrrolinones, Pyrrolidines and Pyrroles. -Ring opening of 2,2-dichlorocyclobutanones such as (I) with primary amines gives the ω,ω-dichlorobutanamides (III). They can be sequentially converted to the pharmacologically interesting pyrrole dyes in a convenient manner. -(VERNIEST, G.; BOTERBERG, S.; BOMBEKE, F.; STEVENS, C. V.; DE KIMPE*,

A short and efficient synthesis is described towards 2-dodecyl-, 2-tetradecyl, 2-(5-tetradecenyl)-and 2-(5,8-tetradecadienyl)cyclobutanones, which are specific markers of gamma-irradiated foodstuffs, e.g. chicken meat and liquid whole egg.

2,2-Dichlorocyclobutanones reacted with various amines to give ring opening leading to 4,4-dichlorobutanamides. These compounds proved to be suitable substrates for the synthesis of 3-pyrrolin-2-ones, 2-pyrrolidinones, pyrrolidines and pyrroles.

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