Publikation: Cycloadditions of 1-aza-2-azoniaallene cations to isothiocyanates
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1999
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El-Gazzar, Abdel-Rahman B.A
Scholten, Kirsten
Guo, Yiping
Weißenbach, Kerstin
Hitzler, Martin
Roth, Gerhard
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Journal of the Chemical Society, Perkin Transactions 1. 1999(14), pp. 1999-2010. ISSN 0300-922X. Available under: doi: 10.1039/A902505G
Zusammenfassung
Isothiocyanates react as S-nucleophiles with 1-aza-2-azoniaallene salts 1 to give different types of 1,3,4-thiadiazolium salts (9, 11, 12) and 1,2,4-triazolium salts (10). Which product is formed, depends on the one hand on the ability of a substituent of the heteroallene salt 1 to undergo a [1,2] shift as a positively charged migrant (generalized Wagner–Meerwein rearrangement) or to act as a cationic leaving group, and on the other hand on Dimroth rearrangement of the initially formed thiadiazolium salt 8 to triazolium salts. The structures of the thiadiazolium salt 9c and the triazolium salt 10d were confirmed by X-ray structural analyses.
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EL-GAZZAR, Abdel-Rahman B.A, Kirsten SCHOLTEN, Yiping GUO, Kerstin WEISSENBACH, Martin HITZLER, Gerhard ROTH, Helmut FISCHER, Johannes JOCHIMS, 1999. Cycloadditions of 1-aza-2-azoniaallene cations to isothiocyanates. In: Journal of the Chemical Society, Perkin Transactions 1. 1999(14), pp. 1999-2010. ISSN 0300-922X. Available under: doi: 10.1039/A902505GBibTex
@article{ElGazzar1999Cyclo-23040,
year={1999},
doi={10.1039/A902505G},
title={Cycloadditions of 1-aza-2-azoniaallene cations to isothiocyanates},
number={14},
issn={0300-922X},
journal={Journal of the Chemical Society, Perkin Transactions 1},
pages={1999--2010},
author={El-Gazzar, Abdel-Rahman B.A and Scholten, Kirsten and Guo, Yiping and Weißenbach, Kerstin and Hitzler, Martin and Roth, Gerhard and Fischer, Helmut and Jochims, Johannes}
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<dcterms:abstract xml:lang="eng">Isothiocyanates react as S-nucleophiles with 1-aza-2-azoniaallene salts 1 to give different types of 1,3,4-thiadiazolium salts (9, 11, 12) and 1,2,4-triazolium salts (10). Which product is formed, depends on the one hand on the ability of a substituent of the heteroallene salt 1 to undergo a [1,2] shift as a positively charged migrant (generalized Wagner–Meerwein rearrangement) or to act as a cationic leaving group, and on the other hand on Dimroth rearrangement of the initially formed thiadiazolium salt 8 to triazolium salts. The structures of the thiadiazolium salt 9c and the triazolium salt 10d were confirmed by X-ray structural analyses.</dcterms:abstract>
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