The Journal of Organic Chemistry

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

JM Larkin, KL Kreuz

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

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被引用次数: 1

摘要

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) ...