This work was supported by the National Science Foundation (CHE-9202152). S. W. thanks the Deutsche Forschungsgemeinschaft for a postdoctoral fellowship (1989–1990).
Novel Structures from Tris(benzocyclobutadieno)cyclohexatriene: Triscyclopropanation and Trisoxacyclopropanation to the First [22.214.171.124.2.1]Hexaannulanes†
Article first published online: 22 DEC 2003
Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 34, Issue 5, pages 563–565, March 20, 1995
How to Cite
Mohler, D. L., Vollhardt, K. P. C. and Wolff, S. (1995), Novel Structures from Tris(benzocyclobutadieno)cyclohexatriene: Triscyclopropanation and Trisoxacyclopropanation to the First [126.96.36.199.2.1]Hexaannulanes. Angew. Chem. Int. Ed. Engl., 34: 563–565. doi: 10.1002/anie.199505631
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 20 SEP 1994
- strained rings
Surprisingly thermally stable, the hexaannulanes 1 can be heated without decomposition to 200 °C (1a) or 180 °C (1b). They are accessible in good yields from tris(benzocyclobutadieno)cyclohexatriene by cyclopropanation with Et2Zn or by epoxidation with 3,3-dimethyl-1,2-dioxacyclopropane, respectively, and were characterized by spectroscopy and X-ray crystallography in the case of 1a for a hexakis(trimethylsilyl) derivative.