Formation of o-nitrosobenzaldehyde from hydrolysis of o-nitrobenzyl tosylate. Evidence of intramolecular nucleophilic interaction

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Abstract

Hydrolysis of o-nitrobenzyl tosylate in CH3CN:H2O (1:1, v/v) gave o- nitrobenzyl alcohol and o-nitrosobenzaldehyde in 1.8 : 1 ratio. Formation of o-nitrosobenzaldehyde indicates that the nitro group participates in the leaving of the tosylate group. o-Nitrosobenzaldehyde was reduced by biological thiols to give o-aminobenzaldehyde. Reaction of o- nitrosobenzaldehyde with 1 tool of benzylamine afforded 3-(N- benzylamino)anthranil (or its tautomer) as a major product.

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Chen, L. J., & Burka, L. T. (1998). Formation of o-nitrosobenzaldehyde from hydrolysis of o-nitrobenzyl tosylate. Evidence of intramolecular nucleophilic interaction. Tetrahedron Letters, 39(30), 5351–5354. https://doi.org/10.1016/S0040-4039(98)01068-5

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