Pyrolysis of annelated hexa- and heptamethylene-tetrazoles: Formation of 9- and 10-membered cyclic carbodiimides

Wentrup, Curt and Vosswinkel, Micheal (2015) Pyrolysis of annelated hexa- and heptamethylene-tetrazoles: Formation of 9- and 10-membered cyclic carbodiimides. Journal of Analytical and Applied Pyrolysis, 117 214-219. doi:10.1016/j.jaap.2015.11.013

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Author Wentrup, Curt
Vosswinkel, Micheal
Title Pyrolysis of annelated hexa- and heptamethylene-tetrazoles: Formation of 9- and 10-membered cyclic carbodiimides
Journal name Journal of Analytical and Applied Pyrolysis   Check publisher's open access policy
ISSN 0165-2370
1873-250X
Publication date 2015-07-14
Year available 2015
Sub-type Article (original research)
DOI 10.1016/j.jaap.2015.11.013
Open Access Status File (Author Post-print)
Volume 117
Start page 214
End page 219
Total pages 6
Place of publication Amsterdam, Netherlands
Publisher Elsevier
Language eng
Abstract A reinterpretation of the spectroscopic data for the products of flash vacuum pyrolysis (FVP) of 8- and 9-membered polymethylenetetrazoles 1, 3, 5, and 7 with annelated benzene rings indicates that these are not cyanamides 2, 4, 6, and 8, but 9- and 10-membered cyclic carbodiimides 9, 10, 11, and 12. FVP of the corresponding tetrazolo[1,5-a]azocine and tetrazolo[1,5-a]azonine derivatives 13 and 17 was investigated by isolation of the products in cryogenic matrices and by matrix photolysis and found to yield 9- and 10-membered cyclic carbodiimides 14 and 18 as transient intermediates en route to indolo[2,3-b]quinoline 15 and dibenzo[b,f]naphthyridine 19.
Keyword Flash vacuum pyrolysis
Matrix isolation
Matrix photolysis
Nitrenes
Imidoylnitrenes
Q-Index Code C1
Q-Index Status Provisional 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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