Action de l'anhydride acétique sur les (aziridinyl-1)-2 tétra-hydropyrannes et sur les dialkylamino-2 tétrahydropyrannes: Influence des substituants de l'azote sur l'orientation de la réaction

The 2-(1-aziridinyl)tetrahydropyrans cannot be obtained by aminolysis of the 2-dialkylaminotetrahydropyrans. These compounds are synthesized by the Hofmann reaction between 2-chlorotetrahydropyrans and ethylenimine. The effect of acetic anhydride on the 2-(1-aziridinyl) and 2-dialkylaminotetrahydropyrans was studied. The 2-dimethylaminotetrahydropyrans were converted into 2-acetoxytetrahydropyrans and dimethylacetamide by cleavage of the carbon-nitrogen bond. Ring opening of the oxygen heterocycle gives the corresponding dialkylacetamides and polymerised products. The 2-(1-aziridinyl)tetrahydropyrans allow the synthesis of the N-(2-tetrahydropyrannyl)-N-(2-acetoxy-ethyl)acetamides. Acetic anhydride ring opens the nitrogen heterocycle.