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II. Reactions

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    Three types of carbohydrate derivatives form carbon-centered radi­cals upon reaction with Cp2TiCl. Halogen-atom abstraction from glycosyl halides pro­duces furanos-1-yl and pyranos-1-yl radicals.1,4–11 Radicals also can be gen­er­ated by abstractive ring opening of ­epoxides.12–19 Finally, Cp2TiCl pro­duces pyranos-1-yl radicals when it reacts with glycosyl 2-pyridyl sulfones.7 An example of the first type of reac­tion is found in eq 2,5,6 one of the second type in eq 3,16 and one of the third in eq 4.7 These radical-forming reactions have the attractive, chemo­selec­tive feature that Cp2TiCl does not affect acetal, ester, or silyl ether protection.5,6

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    This page titled II. Reactions 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.