Abstract
Reaction of a 1-substituted Δ2 -1,2-diazetine with acid chlorides or anhydrides resulted in the derivatives 3a ,b ,f that have been acylated at a ring position. On the other hand, trifluoroacetic anhydride yields a new 1,3,4-oxadiazine 4e under the same conditions. The structure of 4e could be confirmed by X-ray structural analysis. Acylated 1,2-diazetidines of type 3a ,b can be nearly quantitatively transformed into 1,3,4-oxadiazines 4a ,b by thermally induced ring-expansion reactions. Differential scanning calorimetry measurements provide evidence for a monomolecular mechanism in which a strong dependence of the acyl group on the rate of reaction is observed.
Key words
acylations - ring expansion - regioselectivity - heterocycles - imines
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