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AM1 and ab initio calculations were performed on 1-amino-2-methanoyloxirene (cas 157-18-6) (1-amino-2-formyloxirene), the two corresponding oxo carbenes ( ketocarbenes ) resulting from alternative C-O cleavage, and the transition states linking these species. The purpose was to see if delocalization of electron density from the double bond by the push-pull effect of the substituents would stabilize the oxirene system by diminishing its antiaromaticity. This stabilization was not seen: although at the AM1 level the oxirene is a relative minimum, it is merely an inflection point at the HF/3-21G level, and at the HF/6-31G * and MP2(FC)/6-31G * levels the oxirene is merely a transition state.
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