Chemical Reviews, volume 117, issue 5, pages 4562-4623
Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles
Publication type: Journal Article
Publication date: 2017-02-24
Journal:
Chemical Reviews
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 62.1
ISSN: 00092665, 15206890
General Chemistry
Abstract
Flash vacuum pyrolysis (FVP) of azides is an extremely valuable method of generating nitrenes and studying their thermal rearrangements. The nitrenes can in many cases be isolated in low-temperature matrices and observed spectroscopically. NH and methyl, alkyl, aralkyl, vinyl, cyano, aryl and N-heteroaryl, acyl, carbamoyl, alkoxycarbonyl, imidoyl, boryl, silyl, phosphonyl, and sulfonyl nitrenes are included. FVP of triazoloazines generates diazomethylazines and azinylcarbenes, which often rearrange to the energetically more stable arylnitrenes. N2 elimination from monocyclic 1,2,3-triazoles can generate iminocarbenes, 1H-azirines, ketenimines, and cyclization products, and 1,2,4-triazoles are precursors of nitrile ylides. Benzotriazoles are preparatively useful precursors of cyanocyclopentadienes, carbazoles, and aza-analogues. FVP of 5-aryltetrazoles can result in double N2 elimination with formation of arylcarbenes or of heteroarylcarbenes, which again rearrange to arylnitrenes. Many 5-substituted and 2,5-disubstituted tetrazoles are excellent precursors of nitrile imines (propargylic, allenic, or carbenic), which are isolable at low temperatures in some cases (e.g., aryl- and silylnitrile imines) or rearrange to carbodiimides. 1,5-Disubstituted tetrazoles are precursors of imidoylnitrenes, which also rearrange to carbodiimides or add intramolecularly to aryl substituents to yield indazoles and related compounds. Where relevant for the mechanistic understanding, pyrolysis under flow conditions or in solution or the solid state will be mentioned. Results of photolysis reactions and computational chemistry complementing the FVP results will also be mentioned in several places.
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Wentrup C. Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles // Chemical Reviews. 2017. Vol. 117. No. 5. pp. 4562-4623.
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Wentrup C. Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles // Chemical Reviews. 2017. Vol. 117. No. 5. pp. 4562-4623.
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TY - JOUR
DO - 10.1021/acs.chemrev.6b00738
UR - https://doi.org/10.1021/acs.chemrev.6b00738
TI - Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles
T2 - Chemical Reviews
AU - Wentrup, Curt
PY - 2017
DA - 2017/02/24 00:00:00
PB - American Chemical Society (ACS)
SP - 4562-4623
IS - 5
VL - 117
SN - 0009-2665
SN - 1520-6890
ER -
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@article{2017_Wentrup,
author = {Curt Wentrup},
title = {Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles},
journal = {Chemical Reviews},
year = {2017},
volume = {117},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.chemrev.6b00738},
number = {5},
pages = {4562--4623},
doi = {10.1021/acs.chemrev.6b00738}
}
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Wentrup, Curt. “Flash Vacuum Pyrolysis of Azides, Triazoles, and Tetrazoles.” Chemical Reviews, vol. 117, no. 5, Feb. 2017, pp. 4562-4623. https://doi.org/10.1021/acs.chemrev.6b00738.