The Isomerization of Triphenylmethyl Isocyanide: Evidence for a Cationic Chain Mechanism in Polar Solvents

Authors

  • Michael Meier Institut für Organische Chemie und Biochemie Universität Freiburg Albertstrasse 21, D-7800 Freiburg i. Br. (Bundesrepublik Deutschland)
  • Christoph Rüchardt Institut für Organische Chemie und Biochemie Universität Freiburg Albertstrasse 21, D-7800 Freiburg i. Br. (Bundesrepublik Deutschland)

DOI:

https://doi.org/10.2533/chimia.1986.238

Abstract

Triphenylmethyl isocyanide (1) isomerizes to triphenylmethyl cyanide (2) in non-polar solvents at 200-250 °C by a sigmatropic 1,2-rearrangement. To account for the high rate of rearrangement in polar solvents (e.g. acetonitrile) at 60-80°C, a cationic chain mechanism is proposed in contrast to the ion pair return mechanism discussed in the literature.

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Published

1986-08-31

Issue

Vol. 40 No. 7-8 (1986): Forschung/Research

Section

Articles

License

Copyright (c) 1986 Michael Meier

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
M. Meier, C. Rüchardt, Chimia 1986, 40, 238, DOI: 10.2533/chimia.1986.238.