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V. Summary

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    24052

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    Under the proper conditions a phosphatoxy group that is β-related to a radical center will frag­ment to produce an ion pair consisting of a phos­phate anion and a radical cation. This heterolytic fragmentation is favored by polar solvents and formation of radical cations at least as stable as those arising from enol ethers. When the radical center is at C-1 in a pyranoid or furanoid ring, the ion pair recombines to give a new radical in which phosphatoxy group migration to C-1 is accompanied by radical translocation to C-2. If the radical center in a nucleotide is at C-4' and a phosphatoxy group is located at C-3', heterolytic cleavage of the C3'-O bond does not lead to group migration; rather, products arising from hydrogen-atom abstraction, solvent capture, or proton loss are observed.

    This page titled V. 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.

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