On the Reaction of 1-Aza-2-azoniaallene Salts with Carbodiimides

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1993
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Wang, Quanrui
Troll, Carsten
Amer, Atef
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Chemische Berichte. 1993, 126(11), pp. 2519-2524. ISSN 0009-2940. eISSN 1873-3751. Available under: doi: 10.1002/cber.19931261128
Zusammenfassung

1-Aza-2-azoniaallene cations 3, prepared in situ from geminal (chloroalkyl)azo compounds 2, react with carbodiimides 4 to give 4,5-dihydro-5-imino-1H-1,2,4-triazolium salts 7. An X-ray structural analysis was carried out for 71. According to AM1 calculations the cycloaddition of carbodiimides to 1-aza-2-azoniaallene cations occurs in a nonconcerted manner via cyanamidium cations 5 as intermediates. Hetero-Wagner-Meerwein rearrangements of the primary cycloadducts 6 provide the final products 7.

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540 Chemie
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1-Aza-2-azoniaallene cations, Carbodiimides, 1H-1, 2, 4-Triazolium salts
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ISO 690WANG, Quanrui, Carsten TROLL, Helmut FISCHER, Johannes JOCHIMS, Atef AMER, 1993. On the Reaction of 1-Aza-2-azoniaallene Salts with Carbodiimides. In: Chemische Berichte. 1993, 126(11), pp. 2519-2524. ISSN 0009-2940. eISSN 1873-3751. Available under: doi: 10.1002/cber.19931261128
BibTex
@article{Wang1993React-23390,
  year={1993},
  doi={10.1002/cber.19931261128},
  title={On the Reaction of 1-Aza-2-azoniaallene Salts with Carbodiimides},
  number={11},
  volume={126},
  issn={0009-2940},
  journal={Chemische Berichte},
  pages={2519--2524},
  author={Wang, Quanrui and Troll, Carsten and Fischer, Helmut and Jochims, Johannes and Amer, Atef}
}
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    <dcterms:abstract xml:lang="eng">1-Aza-2-azoniaallene cations 3, prepared in situ from geminal (chloroalkyl)azo compounds 2, react with carbodiimides 4 to give 4,5-dihydro-5-imino-1H-1,2,4-triazolium salts 7. An X-ray structural analysis was carried out for 71. According to AM1 calculations the cycloaddition of carbodiimides to 1-aza-2-azoniaallene cations occurs in a nonconcerted manner via cyanamidium cations 5 as intermediates. Hetero-Wagner-Meerwein rearrangements of the primary cycloadducts 6 provide the final products 7.</dcterms:abstract>
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