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Tetrazine

Class of chemical compounds From Wikipedia, the free encyclopedia

Tetrazine is a compound that consists of a six-membered aromatic ring containing four nitrogen atoms with the molecular formula C2H2N4. The name tetrazine is used in the nomenclature of derivatives of this compound. Three core-ring isomers exist: 1,2,3,4-tetrazines, 1,2,3,5-tetrazines, and 1,2,4,5-tetrazines, also known as v-tetrazines, as-tetrazines and s-tetrazines respectively.[1]

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Structure of 1,2,3,4-tetrazine
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Structure of 1,2,4,5-tetrazine

1,2,3,4-Tetrazines

1,2,3,4-Tetrazines are often isolated fused to an aromatic ring system and are stabilized as the dioxide derivatives.

1,2,4,5-Tetrazine

1,2,4,5-Tetrazines are very well known and myriad 3,6-disubstituted 1,2,4,5-tetrazines are known.[2] These materials are of use[vague] in the area of energetic chemistry.[citation needed]

Heavily substituted tetrazines form the verdazyls, a family of stable radicals.[3]

Protected tetrazines are strong acetylene acceptors in Diels-Alder equilibria. For example, dipyridinyl 1,2,4,5-tetrazine abstracts acetylene from norbornadiene to cyclopentadiene and a pyridazine:[4]

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With norbornadiene fused to an arene the reaction stops at an intermediary stage.[5]

See also

  • 6-membered rings with one nitrogen atom: pyridine
  • 6-membered rings with two nitrogen atoms: diazines
  • 6-membered rings with three nitrogen atoms: triazines
  • 6-membered rings with five nitrogen atoms: pentazine
  • 6-membered rings with six nitrogen atoms: hexazine

References

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