Abstract
The reaction of 2 - dimethylamino - 3,3 - dimethyl - 1 - azirine 1 with carboxylic acids 2a-e at room temperature in inert solvents generates rearranged 1:1 adducts in 65–92% yields. These adducts are N-acyl derivatives of 2-amino, -N,N dimethyl-isobutyramide 3a-e resulting from 1,2 addition of the acid followed by 1,2 ring cleavage and transfer of an acyl group. Cyclic enolizable 1,3 diketones 4a-c react similarly with 1 to yield the corresponding rearranged 1:1 adducts 5a-c, whereas acyclic diketones or ethyl acetoacetate are inert under comparable experimental conditions.
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