Tetrahedron

Rearrangements and cyclizations—XVI: Ring-opening reactions of 1, 1-diacetylcyclopropane with hydrazine and hydroxylamine derivatives as the novel synthesis of β …

NS Zefirov, SI Kozhushkov, TS Kuznetsova

Index: Zefirov, Nikolai S.; Kozhushkov, Sergei I.; Kuznetsova, Tamara S. Tetrahedron, 1982 , vol. 38, # 11 p. 1693 - 1697

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Citation Number: 49

Abstract

The reactions of 1, 1-diacetylcyclopropane (1) with a number of hydrazine and hydroxylamine derivatives proceed via cyclopropane ring opening with incorporation of external nucleophile (solvent) to give the 4-β-X-ethyl derivatives of 3, 5-dimethylpyrazoles and-isoxazoles, a novel route to these heterocycles. This ring cleavage occurs especially smoothly in water as a solvent. A rationale for this unusually mild nucleophilic ...