Tetrazine

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Not to be confused with tetrazene.
Structure of 1,2,3,4-tetrazine
Structure of 1,2,4,5-tetrazine

Tetrazine is an unstable 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.

1,2,3,4-Tetrazines[edit]

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[edit]

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

The compound 3,6-di-2-pyridyl-1,2,4,5-tetrazine'[2] has two pyridine substituents and is of importance as a reagent in Diels-Alder reactions. It reacts with norbornadiene in a sequence of one DA reaction and two retro-DA reactions to cyclopentadiene and a pyridazine with exchange of an acetylene unit:

reaction of norbornadiene with 3,6-di-2-pyridyl-1,2,4,5-tetrazine

With norbornadiene fused to an arene the reaction stops at an intermediary stage [3]

See also[edit]

  • 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 six nitrogen atoms: hexazine

References[edit]

  1. ^ (see United States Patent 6645325)
  2. ^ Datasheet: Link
  3. ^ π-Bond Screening in Benzonorbornadienes: The Role of 7-Substituents in Governing the Facial Selectivity for the Diels-Alder Reaction of Benzonorbornadienes with 3,6-Di(2-pyridyl)-s-Tetrazine. Ronald N. Warrener and Peter A. Harrison Molecules 2001, 6, 353–369 Online Article