The Journal of Organic Chemistry

Thermal rearrangement of. beta.-nitro nitrates to dinitro alcohols

JM Larkin, KL Kreuz

Index: Larkin,J.M.; Kreuz,K.L. Journal of Organic Chemistry, 1972 , vol. 37, p. 3079 - 3085

Full Text: HTML

Citation Number: 1

Abstract

The decomposition of p-nitroalkyl nitrates in dilute hydrocarbon or halocarbon solution follows first-order kinetics (idfa= 38-40 kcal mol-') to give dinitro or bromonitro alcohols derived from a 1, 5 intramolecular hydrogen shift. For instance, l-nitro-2-methyl-2-pentyl nitrate (5) rearranges at 130" in chlorobenzene to 1, 5-dinitro-2-methyl-2-pentanol (13) in 86% yield; in refluxing CBrCb, 5 is converted to l-nitro-5-bromo-2-methyl-2-pentanol (13a) ...

Related Articles:

Full, Reactive Solubilization of Humin Byproducts by Alkaline Treatment and Characterization of the Alkali-Treated Humins Formed

[Clark, James H.; Cork, David G.; Gibbs, Hugh W. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983 , p. 2253 - 2258]

1-Benzyl-1, 4-dihydronicotinamide as a reagent for replacing aliphatic nitro groups by hydrogen. An electron-transfer chain reaction

[Ono; Tamura; Kaji Journal of the American Chemical Society, 1983 , vol. 105, # 12 p. 4017 - 4022]

Bifunctional Heterogeneous Catalysis of Silica–Alumina??Supported Tertiary Amines with Controlled Acid–Base Interactions for Efficient 1, 4??Addition Reactions

[Motokura, Ken; Tanaka, Satoka; Tada, Mizuki; Iwasawa, Yasuhiro Chemistry - A European Journal, 2009 , vol. 15, # 41 p. 10871 - 10879]

Enzymic kinetic resolution of. alpha.-nitro. alpha.-methyl carboxylic acids

[Lalonde, James J.; Bergbreiter, David E.; Wong, C.-H. Journal of Organic Chemistry, 1988 , vol. 53, # 10 p. 2323 - 2327]

More Articles...