The mechanism of Sandmeyer's cyclization reaction by electrospray ionization mass spectrometry

Rapid Commun Mass Spectrom. 2011 Feb 15;25(3):423-8. doi: 10.1002/rcm.4869.

Abstract

Using electrospray ionization (tandem) mass spectrometry (ESI-MS(/MS)) spectrometric experiments, the Sandmeyer reaction was monitored on-line, and key intermediates were intercepted and characterized for the first time. The mechanistic information provided by on-line ESI-MS(/MS) is in accordance with Sandmeyer's proposal, and was made possible by coupling a microreactor on-line to the ESI ion source, which allowed reactions to be screened from 0.7-2.0 s, identifying and characterizing all intermediates that were formed and consumed during the reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetanilides / chemistry
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry*
  • Models, Chemical*
  • Spectrometry, Mass, Electrospray Ionization / methods*
  • Tandem Mass Spectrometry

Substances

  • Acetanilides
  • Heterocyclic Compounds