Tetrazine

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

1,2,3,4-Tetrazines are often isolated fused to an aromatic ring system and are stablized 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. [(see United States Patent 6645325)] These materials are of use in the area of energetic chemistry.

The compound 3,6-di-2-pyridyl-1,2,4,5-tetrazine [Datasheet: [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/403547 Link] ] 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 reactions and two retro-DA reactions to cyclopentadiene and a pyridazine with exchange of an acetylene unit:

:

With norbornadiene fused to an arene the reaction stops at an intermediary stage ["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 [http://www.mdpi.org/molecules/papers/60400353.pdf Online Article] ]

ee also

* 6-membered rings with one nitrogen atom:pyridines
* 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


Wikimedia Foundation. 2010.

Игры ⚽ Нужно сделать НИР?

Look at other dictionaries:

  • Tetrazine — sind eine Stoffklasse heteroaromatischer Sechsringe mit vier Stickstoffatomen im Ring und damit eine Untergruppe der Azine. Von den drei möglichen Isomeren ist insbesondere das 1,2,4,5 Tetrazin wichtig. 1,2,3,4 Tetrazin und 1,2,3,5 Tetrazin… …   Deutsch Wikipedia

  • Tetrazine — Tet*raz ine, n. Also in in . [Tetrazo + ine.] (Chem.) A hypothetical compound, {C2H2N4} which may be regarded as benzene with four {CH} groups replaced by nitrogen atoms; also, any of various derivatives of the same. There are three isomeric… …   The Collaborative International Dictionary of English

  • tétrazine — ● tétrazine nom féminin Composé hétérocyclique C2H2N4, résultant du remplacement de quatre groupes CH du benzène par des atomes d azote …   Encyclopédie Universelle

  • Tétrazine — Les trois isomères de la tétrazine : de gauche à droite la 1,2,3,4 tétrazine, la 1,2,4,5 tétrazine et la 1,2,3,5 tétrazine Une tétrazine est un composé organique instable constitué d un noyau aromatique à six atomes contenant quatre atomes d …   Wikipédia en Français

  • Tetrazine — Azine Les Azines ou pyridines sont une famille de composés organiques hétérocycliques insaturés, possédant un cycle de six atomes : cinq de carbone et un d azote. L azine la plus simple est la pyridine. Pyridine …   Wikipédia en Français

  • tetrazine — tetrazinas statusas T sritis chemija apibrėžtis Šešianaris heterociklinis junginys. formulė C₂H₂N₄ atitikmenys: angl. tetrazine rus. тетразин …   Chemijos terminų aiškinamasis žodynas

  • tetrazine — noun Any six membered heterocycle having two carbon atoms, four nitrogen atoms and three double bonds …   Wiktionary

  • tetrazine — tet·ra·zine …   English syllables

  • tetrazine — ˈte.trəˌzēn, zə̇n noun ( s) Etymology: International Scientific Vocabulary tetraz + ine 1. : any of three isomeric parent compounds C2H2N4 that may be regarded as benzene with four methylidyne groups replaced by nitrogen atoms; especially : the… …   Useful english dictionary

  • C2H2N4 — Tetrazine Tet*raz ine, n. Also in in . [Tetrazo + ine.] (Chem.) A hypothetical compound, {C2H2N4} which may be regarded as benzene with four {CH} groups replaced by nitrogen atoms; also, any of various derivatives of the same. There are three… …   The Collaborative International Dictionary of English

Share the article and excerpts

Direct link
… Do a right-click on the link above
and select “Copy Link”