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Synlett 1997; 1997(1): 27-28
DOI: 10.1055/s-1997-702
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Reaction of Hydrazones with Methoxy(tosyloxy)iodobenzene (MTIB): Tosylate Formation under Oxidative Conditions

Christopher A. Ramsden* , Helen L. Rose
  • *Department of Chemistry, Keele University, Keele, Staffordshire ST5 5BG, England
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Publication Date:
22 March 2004 (online)

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Treatment of aromatic hydrazones 1 containing electron-withdrawing, reduction sensitive substituents with MTIB gives the corresponding tosylates 2 in high yield. When the tosylate is particularly reactive the thermodynamically more stable methyl ether 3 is isolated. Analogous reactions with DAIB give acetates 4 in high yield. Dialkyl hydrazones give olefinic products (e.g. 7 and 8). (+)-Camphor hydrazone 1k with either MTIB or DAIB gives both camphene 12 (major product) and tricyclene 11 (minor product) suggesting that a carbene pathway accounts for some of the material formed in these oxidations.

hydrazones - tosylates - methoxy(tosyloxy)iodobenzene - diacetoxyiodobenzene - lead tetraacetate