The Journal of Organic Chemistry

Transformation of nitrimines to acetylenes and allenes. 1, 3 Rearrangement of N-nitroenamines to C-nitro compounds

G Buechi, H Wuest

文献索引：Buechi,G.; Wueest,H. Journal of Organic Chemistry, 1979 , vol. 44, p. 4116 - 4120

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被引用次数: 35

摘要

Nitrimines, prepared from ketoximes and nitrous acid, can be converted to acetylenes and allenes by treatment with excess acetic anhydride in the presence of pyridine at reflux. With 4-(dimethy1amino) pyridine as catalyst, most fragmentations proceed at room temperature. Consecutive treatment of nitrimines with strong bases and aqueous acid allows their isomerization to the less stable N-nitroenamines which on storage revert to the parent ...