Tetrahedron Letters

Novel oxidative rearrangement of β, γ-unsaturated ketone hydrazones on iodination in base

ME Jung, GL Hatfield

Index: Jung, Michael E.; Hatfield, Gregory L. Tetrahedron Letters, 1982 , vol. 23, # 39 p. 3991 - 3994

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Citation Number: 3

Abstract

... NOVEL OXIDATIVE REARRANGEMENT OF Y-UNSATURATED KETONE HYDRAZONES ON IODINATION IN BASE Michael E. Jung *1 and ... carbonium ion 12 either directly (path b) or with double bond participation ma the cyclopropylcarbinyl cation 11 (path a). Removal of a proton from 12 with triethylamine would afford the 3993 II Me -NH 2 Me N-NHI Me 2 Me + Me N2 1 2 _ -HI 1 2 -N2 / Et 3N / Et3N / ib Me Me Me Me Me 3 7 8 9 10 -H+ ba Et3 Me e I e I Me I ...