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VII. Summary

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    Radical reaction of a carboxylic acid ester of N-hydroxypyridine-2-thi­one causes the weak N–O bond to fragment to produce acyloxy and 2-pyrid­yl­thiyl radi­cals. The acyloxy radical then loses carbon dioxide to form a carbon-centered, carbohydrate radical. Carbon-centered radicals produced in this way abstract hydrogen atoms from highly reactive donors, such as thiols, and they combine with 2-pyridylthiyl radicals formed in the initial N–O bond homolysis. These carbo­hy­drate radicals also can add to α,β-unsatur­ated esters and amides, to compounds with phenyl­sul­fonyl- or nitro-substituted multiple bonds, and to protonated aromatic amines. ­Photolysis of acet­ylated N-hy­droxy­pyridine-2-thione provides a source of methyl radicals that react readily with tellurium-containing carbohydrates to produce carbohydrate radicals.

    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.

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