Cycloadditions of 1-aza-2-azoniaallene cations to isothiocyanates

El-Gazzar, Abdel-Rahman B.A; Scholten, Kirsten; Guo, Yiping; Weißenbach, Kerstin; Hitzler, Martin; Roth, Gerhard; Fischer, Helmut; Jochims, Johannes

Cycloadditions of 1-aza-2-azoniaallene cations to isothiocyanates

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Datum

1999

Autor:innen

El-Gazzar, Abdel-Rahman B.A

Scholten, Kirsten

Guo, Yiping

Weißenbach, Kerstin

Hitzler, Martin

Roth, Gerhard

Fischer, Helmut

Jochims, Johannes

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

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.

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

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/A902505G

BibTex

@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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