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How nucleophilic are diazo compounds?

Thorsten Bug1, Manfred Hartnagel, Clemens Schlierf

  • 1Department Chemie der Ludwig-Maximilians-Universität München Butenandtstrasse 5 - 13 (Haus F), 81377 München, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 4, 2003
PubMed
Summary

This study quantifies the nucleophilicity of diazo compounds reacting with benzhydryl cations. Their reactivity spans ten orders of magnitude, similar to alkenes and enamines.

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Rolf Huisgen (1920-2020).

Angewandte Chemie (International ed. in English)·2020

Area of Science:

  • Organic Chemistry
  • Reaction Kinetics

Background:

  • Benzhydryl cations are electrophiles.
  • Diazo compounds are versatile nucleophiles.

Purpose of the Study:

  • To investigate the kinetics of benzhydryl cation reactions with diazo compounds.
  • To determine nucleophilicity parameters (N) and slope parameters (s) for diazo compounds.
  • To compare the nucleophilicities of diazo compounds with other pi systems.

Main Methods:

  • Photometric investigation in dichloromethane.
  • Kinetic analysis using the equation log k (20 degrees C)=s (E+N).

Main Results:

  • Nucleophilicity parameters (N) and slope parameters (s) were derived for eight diazo compounds.

Related Experiment Videos

  • The nucleophilic reactivities of diazo compounds span over ten orders of magnitude.
  • Diazo compound reactivity was compared to alkenes, arenes, silyl enol ethers, and silyl ketene acetals.

    • Conclusions:

    • Diazo compounds exhibit a wide range of nucleophilicities, comparable to styrene and enamines.
    • The rate-determining step is the electrophilic attack at the diazo-carbon atom.
    • The study provides valuable kinetic data for understanding diazo compound reactivity.