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Attempts to iodinate the fluorophenylisoxazoline shown led to an empirical demonstration of the rather profound electronic differences between the isoxazoline moiety and its bioisosteric predecessor, the oxazolidinone ring system. Whereas iodine monochloride smoothly reacts with the oxazolidinone intermediate to give the targeted para iodo derivative, the corresponding isoxazoline fails to react, even under forcing conditions.
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