Preparation of unsymmetrically labeled hydroperoxides. A hydroxamate ester-nitrosation approach

NA Porter, SE Caldwell, JR Lowe

文献索引：Porter, Ned A.; Caldwell, Sarah E.; Lowe, Jennifer R. Journal of Organic Chemistry, 1998 , vol. 63, # 16 p. 5547 - 5554

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被引用次数: 17

摘要

Reaction of O-tertiary alkyl arylhydroxamate esters with nitrosyl chloride gives O-tertiary alkyl aryl peresters that can be hydrolyzed to the hydroperoxide. If the hydroxamate ester carbonyl oxygen or nitrosyl chloride is labeled with 18O, the label appears in the product hydroperoxide's terminal oxygen. This strategy, which derives from the pioneering work of Koenig, permits the preparation of a variety of (2-18O) hydroperoxides, including tertiary ...