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Issue 20, 1999
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Non-photochemical rearrangements of o-nitrobenzyl compounds

Abstract

Three rearrangements of 2-nitrobenzyl compounds with increasingly complex structural changes are described. The first is a remarkably facile conversion of 2-nitrobenzyl triflate to 2-nitrosobenzaldehyde. The second is an unexpected formation of 1-acetyl-2,1-benzisoxazolone 7 during attempted preparation of the tert-butyl ester of O-acetyl 2-nitromandelic acid. The third, found in the reaction of 2-nitrobenzaldehyde cyanohydrin TMS ether 10 with cyclic secondary amines, results in oxidative cyanation of the position alpha to the amino group, giving the novel N-arylamino-α-cyanoamines 12a–e.

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Article type: Paper
DOI: 10.1039/A904676C
Citation: J. Chem. Soc., Perkin Trans. 1, 1999, 2977-2982
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    Non-photochemical rearrangements of o-nitrobenzyl compounds

    J. E. T. Corrie, M. J. Gradwell and G. Papageorgiou, J. Chem. Soc., Perkin Trans. 1, 1999, 2977
    DOI: 10.1039/A904676C

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