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

  • Chen L
  • Burka L
  • 5


    Mendeley users who have this article in their library.
  • 16


    Citations of this article.


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.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document


  • Ling Jen Chen

  • Leo T. Burka

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free