The Journal of Organic Chemistry

Reaction of dinitrogen tetraoxide with hydrophilic olefins: synthesis of citric and 2-hydroxy-2-methylbutanedioic acids

JB Wilkes, RG Wall

Index: Wilkes, John B.; Wall, Robert G. Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 247 - 250

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Citation Number: 14

Abstract

Liquid olefins typically react with NzO4 by free-radical reactions to form dinitro and nitronitrite derivatives. Introduction of hydrophilic substituents into 1-olefins altered the course of the reaction of the olefins with N? 04 in aqueous HN03. Citric acid was formed in 64 mol% yield by the reaction of 3-methylene-l, 5-pentanediol wlth Nz04 in aqueous HNOB. Similarly, 2-hydroxy-2-methylbutanedioic acid was made from 3-methyl-3-buten-1-01 in ...