This report describes the hydrodediazoniation of dry arenediazonium o-benzenedisulfonimides with hydrogen peroxide in THF at reflux. The new procedure is general, giving positive results in the presence of both electron-donating and electron-withdrawing substituents. Furthermore, it does not suffer from steric effects and always gives the pure reduction products in excellent yields (15 examples, average yield = 93%). All the reactions show over 90% recovery of o-benzenedisulfonimide that can be reused to prepare the salts. The collateral proofs we performed led us to hypothesize, for this reaction, a free-radical chain mechanism in which hydrogen peroxide is the exclusive hydrogen source in the arenes Ar-H.

Hydrodediazoniation of Dry Arenediazonium o-Benzenedisulfonimides with Hydrogen Peroxide

BARBERO, Margherita;DEGANI, Jacopo;DUGHERA, Stefano;FOCHI, Rita
2004-01-01

Abstract

This report describes the hydrodediazoniation of dry arenediazonium o-benzenedisulfonimides with hydrogen peroxide in THF at reflux. The new procedure is general, giving positive results in the presence of both electron-donating and electron-withdrawing substituents. Furthermore, it does not suffer from steric effects and always gives the pure reduction products in excellent yields (15 examples, average yield = 93%). All the reactions show over 90% recovery of o-benzenedisulfonimide that can be reused to prepare the salts. The collateral proofs we performed led us to hypothesize, for this reaction, a free-radical chain mechanism in which hydrogen peroxide is the exclusive hydrogen source in the arenes Ar-H.
14
2386
2390
reductions - diazonium compounds - radical reactions - sulfur
M. BARBERO; I. DEGANI; S. DUGHERA; R. FOCHI
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1619
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact