C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles

Wentrup, Curt, Becker, Jurgen and Diehl, Manfred (2015) C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles. Journal of Organic Chemistry, 80 14: 7144-7149. doi:10.1021/acs.joc.5b01007


Author Wentrup, Curt
Becker, Jurgen
Diehl, Manfred
Title C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles
Formatted title
C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
1520-6904
Publication date 2015-07-17
Year available 2015
Sub-type Article (original research)
DOI 10.1021/acs.joc.5b01007
Open Access Status Not yet assessed
Volume 80
Issue 14
Start page 7144
End page 7149
Total pages 6
Place of publication Washington, United States
Publisher American Chemical Society
Collection year 2016
Language eng
Formatted abstract
2-Phenyl-5-(phenylethynyl)tetrazole 44 provides a new entry to the C15H10 energy surface. Flash vacuum pyrolysis of 44 using the falling solid flash vacuum pyrolysis (FS-FVP) method afforded cyclopenta[def]phenanthrene 31 and cyclopenta[jk]fluorene 52 as the principal products. The products are explained in terms of the formation of N-phenyl-C-phenylethynylnitrile imine/(phenylazo)(phenylethynyl)carbene 45 and its cyclization to 3-(phenylethynyl)-3H-indazole 46b. Pyrolytic loss of N2 from 46b generates C15H10 intermediate 48. Cyclization of 48 to a dibenzocycloheptatetraene derivative and further rearrangements with analogies in the chemistry of phenylcarbene and the naphthylcarbenes leads to the final products. Similar pyrolysis of 2-phenyl-5-styryltetrazole 43 afforded 3-styrylindazole 58, which on further pyrolysis eliminated N2 to generate 3- and 2-phenylindenes 61 and 62 via C15H12 intermediates.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2016 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Mon, 17 Aug 2015, 15:50:15 EST by Prycilla Rehm on behalf of School of Chemistry & Molecular Biosciences