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

Overview of attention for article published in Journal of Organic Chemistry, June 2015
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Title
C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles
Published in
Journal of Organic Chemistry, June 2015
DOI 10.1021/acs.joc.5b01007
Pubmed ID
Authors

Curt Wentrup, Jürgen Becker, Manfred Diehl

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[fg]fluorene 52 as the principal products. The products are explained in terms of 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 the C15H10 intermediate 48. Cyclization of 48 to a dibenzocycloheptatetraene derivative and further rearrangements with analogies in the chemistry of phenylcarbene and the naphthylcarbenes lead 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.

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Mendeley readers

Mendeley readers

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Geographical breakdown

Country Count As %
Unknown 10 100%

Demographic breakdown

Readers by professional status Count As %
Researcher 4 40%
Student > Ph. D. Student 3 30%
Professor 1 10%
Student > Master 1 10%
Other 1 10%
Other 0 0%
Readers by discipline Count As %
Chemistry 7 70%
Chemical Engineering 1 10%
Engineering 1 10%
Unknown 1 10%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 1. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 28 June 2015.
All research outputs
#20,657,128
of 25,377,790 outputs
Outputs from Journal of Organic Chemistry
#26,833
of 28,613 outputs
Outputs of similar age
#203,181
of 278,181 outputs
Outputs of similar age from Journal of Organic Chemistry
#72
of 95 outputs
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