ChemInform Abstract: Preparation of 2-Substituted Naphth[2,3-d]oxazole-4,9-diones via a Radical Chain Process.
Abstract
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ChemInform Abstract
Reaction of chloromethylnaphthoxazoledione (I), prepared by bromination—halogen exchange reaction from methylnaphthoxazoledione, with nitroalkane anions proceeds via an SRN1 mechanism to provide access to ethylenic naphthoxazolediones (III), (VI), (VIII)/(IX) and (XI). The reaction mechanism is confirmed by use of radical chain inhibition experiments. Reaction with unsymmetrical nitroalkanes (VII) and (X) proceeds with high to excellent E-selectivity.
