Azulene–Naphthalene‐Type Rearrangements in Benz[a]azulene and Cyclohepta[b]indole |
| |
| Authors: | Prof Dr Curt Wentrup Dr Jürgen Becker |
| |
| Institution: | 1. http://researchers.uq.edu.au/researcher/3606;2. School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Australia;3. Fachbereich Chemie der Philipps-Universit?t, Marburg, Germany |
| |
| Abstract: | Flash vacuum pyrolysis (FVP) of benza]azulene yields phenanthrene and 2‐ethynylbiphenyl. FVP of cycloheptab]indole similarly yields phenanthridine and 2‐cyanobiphenyl. The reversibility of the reactions is demonstrated by FVP of 2‐ethynylbiphenyl and 2‐isocyanobiphenyl. All the observed reactions are in accord with the norcaradiene–vinylidene mechanism of the azulene–naphthalene rearrangement, whereas other proposed mechanisms are ruled out. |
| |
| Keywords: | arenes flash vacuum pyrolysis hetarenes reaction mechanisms rearrangement |
|
