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

…, AB Reitz, BA Duhl-Emswiler

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

Full Text: HTML

Citation Number: 169

Abstract

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- ...