Tetrazine

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]

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]

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.^[5]

References

^ Alvarez-Builla, Julio; Jose Vaquero, Juan; Barluenga, José (2011). Modern Heterocyclic Chemistry. Wiley-VCH. p. 1778. ISBN 978-3527332014.
^ (see United States Patent 6645325)
^ Hicks, Robin G. (2010). "Verdazyls and related radicals containing the hydrazyl [R₂N–NR] group". In Hicks, Robin G. (ed.). Stable Radicals. Wiley. pp. 246–264. ISBN 978-0-470-77083-2.
^
- Dalkılıç, Erdin, and Arif Daştan. "Synthesis of cyclopentadiene derivatives by retro-Diels–Alder reaction of norbornadiene derivatives." Tetrahedron 71.13 (2015): 1966-1970.
- Dalkılıç, Erdin, et al. "Novel and versatile protocol for the preparation of functionalized benzocyclotrimers." Tetrahedron Letters 50.17 (2009): 1989-1991.
^ 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

[1] Alvarez-Builla, Julio; Jose Vaquero, Juan; Barluenga, José (2011). Modern Heterocyclic Chemistry. Wiley-VCH. p. 1778. ISBN 978-3527332014.

[2] (see United States Patent 6645325)

[Radicals-3] Hicks, Robin G. (2010). "Verdazyls and related radicals containing the hydrazyl [R₂N–NR] group". In Hicks, Robin G. (ed.). Stable Radicals. Wiley. pp. 246–264. ISBN 978-0-470-77083-2.

[4] 
Dalkılıç, Erdin, and Arif Daştan. "Synthesis of cyclopentadiene derivatives by retro-Diels–Alder reaction of norbornadiene derivatives." Tetrahedron 71.13 (2015): 1966-1970.
Dalkılıç, Erdin, et al. "Novel and versatile protocol for the preparation of functionalized benzocyclotrimers." Tetrahedron Letters 50.17 (2009): 1989-1991.

[5] Dalkılıç, Erdin, and Arif Daştan. "Synthesis of cyclopentadiene derivatives by retro-Diels–Alder reaction of norbornadiene derivatives." Tetrahedron 71.13 (2015): 1966-1970.

[6] Dalkılıç, Erdin, et al. "Novel and versatile protocol for the preparation of functionalized benzocyclotrimers." Tetrahedron Letters 50.17 (2009): 1989-1991.

[5] 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

[1]

[2]

[3]

[4]

[5]

Tetrazine

1,2,3,4-Tetrazines

1,2,4,5-Tetrazine

See also

References

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