PMID- 26086716
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20150922
LR  - 20150718
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 80
IP  - 14
DP  - 2015 Jul 17
TI  - C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes 
      by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles.
PG  - 7144-9
LID - 10.1021/acs.joc.5b01007 [doi]
AB  - 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.
FAU - Wentrup, Curt
AU  - Wentrup C
AD  - daggerFachbereich Chemie der Philipps-Universitat Marburg, D-35037 Marburg, Germany.
AD  - double daggerSchool of Chemistry and Molecular Biosciences, The University of Queensland, 
      Brisbane, Qld 4072, Australia.
FAU - Becker, Jurgen
AU  - Becker J
AD  - daggerFachbereich Chemie der Philipps-Universitat Marburg, D-35037 Marburg, Germany.
FAU - Diehl, Manfred
AU  - Diehl M
AD  - daggerFachbereich Chemie der Philipps-Universitat Marburg, D-35037 Marburg, Germany.
LA  - eng
PT  - Journal Article
DEP - 20150626
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
EDAT- 2015/06/19 06:00
MHDA- 2015/06/19 06:01
CRDT- 2015/06/19 06:00
PHST- 2015/06/19 06:00 [entrez]
PHST- 2015/06/19 06:00 [pubmed]
PHST- 2015/06/19 06:01 [medline]
AID - 10.1021/acs.joc.5b01007 [doi]
PST - ppublish
SO  - J Org Chem. 2015 Jul 17;80(14):7144-9. doi: 10.1021/acs.joc.5b01007. Epub 2015 
      Jun 26.