Stereochemistry of the Wittig reaction. Effect of nucleophilic groups in the phosphonium ylide

…, AB Reitz, BA Duhl-Emswiler

文献索引：Maryanoff,B.E.; Reitz,A.; Duhl-Emswiler,B. Journal of the American Chemical Society, 1985 , vol. 10, p. 217

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被引用次数: 169

摘要

Summary, Conclusions, and Toxicological Implications We have shown that N2O4 readily nitrosates organic hydroperoxides in solution, giving pernitrite esters that ultimately rearrange to give alkyl nitrates as major products. Nitrates are susceptible to acid-catalyzed decomposition to nitrous acid; the potential for damage by nitrous acid in a biological system is well-known. 46 In addition, a significant fraction of the initially formed pernitrite (ca. 20- ...