Tri‐tert‐butylazete—The First Kinetically Stabilized Azacyclobutadiene

Vogelbacher, Uwe‐Josef; Regitz, Manfred; Mynott, Richard

doi:10.1002/anie.198608421

Angewandte Chemie International Edition

Explore this journal >

Explore this journal >

Communication

Tri-tert-butylazete—The First Kinetically Stabilized Azacyclobutadiene^†

Authors

Dipl.-Chem. Uwe-Josef Vogelbacher,
1. Fachbereich Chemie der Universität, Erwin-Schrödinger-Strasse, D-6750 Kaiserslautern (FRG)
Search for more papers by this author
Prof. Dr. Manfred Regitz,
Corresponding author
1. Fachbereich Chemie der Universität, Erwin-Schrödinger-Strasse, D-6750 Kaiserslautern (FRG)
- Fachbereich Chemie der Universität, Erwin-Schrödinger-Strasse, D-6750 Kaiserslautern (FRG)
Search for more papers by this author
Dr. Richard Mynott
1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-4330 Mülheim an der Ruhr (FRG)
Search for more papers by this author

First published: September 1986Full publication history
DOI: 10.1002/anie.198608421 View/save citation
Cited by (CrossRef): 34 articles Check for updates
- Citing literature

^†
Syntheses with Cyclobutadienes, Part 16. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.—Part 15: H. Wingert, G. Maas, M. Regitz, Tetrahedron, in press.

Abstract

The antiarene 1 is remarkably stable. It was prepared as the first kinetically stabilized (electronically pure) azacyclobutadiene. 1 tolerates several days' heating at 100°C in toluene! The valence isomerism 1A⇄1B is immediately detectable by temperature-dependent ₁₃C-NMR spectroscopy.

Continue reading full article