Azulene–naphthalene-type rearrangements in Benz[a]azulene and Cyclohepta[b]indole

Wentrup, Curt and Becker, Jürgen (2016) Azulene–naphthalene-type rearrangements in Benz[a]azulene and Cyclohepta[b]indole. Chemistry - A European Journal, 22 39: 13835-13839. doi:10.1002/chem.201603389


Author Wentrup, Curt
Becker, Jürgen
Title Azulene–naphthalene-type rearrangements in Benz[a]azulene and Cyclohepta[b]indole
Formatted title
Azulene–naphthalene-type rearrangements in Benz[a]azulene and Cyclohepta[b]indole
Journal name Chemistry - A European Journal   Check publisher's open access policy
ISSN 1521-3765
0947-6539
Publication date 2016-08-18
Year available 2016
Sub-type Article (original research)
DOI 10.1002/chem.201603389
Open Access Status Not yet assessed
Volume 22
Issue 39
Start page 13835
End page 13839
Total pages 6
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Language eng
Abstract Flash vacuum pyrolysis (FVP) of benz[a] azulene yields phenanthrene and 2-ethynylbiphenyl. FVP of cyclohepta[b] 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.
Formatted abstract
Flash vacuum pyrolysis (FVP) of benz[a]azulene yields phenanthrene and 2-ethynylbiphenyl. FVP of cyclo-hepta[b]indole similarly yields phenanthridine and 2-cyanobiphenyl. The reversibility of the reactions is demonstrated by FVP of 2-ethynylb iphenyl 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.
Keyword Flash vacuum pyrolysis (FVP)
Activation energy
Thermal isomerization
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID CW 1328
DP0770863
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 19 Aug 2016, 19:31:58 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences