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VII. Summary

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    24558

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    Carbon-centered radicals add to carbon–nitrogen double bonds in oxime ethers, hydrazones, ketonitrones, and protonated heteroaromatics. These reactions are regiospecific with addition occurring to the carbon atom in the double bond. The majority of such reactions involve oxime ethers and usually result in formation of a new ring. These cyclization reactions often are quite stereoselective. This is particularly true if an O-isopropylidene group is near the reactive center, in which case the nitrogen-containing substituent and the O-isopropylidene group in the product are on opposite sides of the new ring. Radical addition to protonated heteroaromatics is different from addition to other compounds containing carbon–nitrogen multiple bonds because addi­tion is always followed by hydrogen-atom abstraction that rearomatizes the ring.

    This page titled VII. Summary is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Roger W. Binkley and Edith R. Binkley.