Carboni-Lindsey reaction

The Carboni-Lindsey reaction is a name reaction in organic chemistry and was first published in 1959 by RA Carboni and RV Lindsey Jr. The reaction allows the synthesis of pyridazine from tetrazine and an alkene .

Overview reaction

1,2,4,5-Tetrazine reacts with an alkene, releasing nitrogen and hydrogen to form a pyridazine:

Reaction mechanism

The reaction mechanism is described in the literature and involves a Diels-Alder reaction between the tetrazine and a dienophile :

First, a Diels-Alder reaction takes place between the 1,2,4,5-tetrazine ( 1 ) and the dienophile, in this case the 1,3-diene ( 2 ). The pyridazine ( 3 ) is then split off and released from nitrogen and hydrogen .

Individual evidence

^ RA Carboni and RV Lindsey Jr .: Reactions of Tetrazines with Unsaturated Compounds. A New Synthesis of Pyridazines In: J. Am. Chem. Soc. 81 (16), 1959, pp. 4342-4346, doi: 10.1021 / ja01525a060 .
^ Z. Wang: Comprehensive organic name reactions and reagents Volume 1 . John Wiley, Hoboken (NJ) 2009, ISBN 978-0-470-28662-3 , pp. 606-610 .

[1] RA Carboni and RV Lindsey Jr .: Reactions of Tetrazines with Unsaturated Compounds. A New Synthesis of Pyridazines In: J. Am. Chem. Soc. 81 (16), 1959, pp. 4342-4346, doi: 10.1021 / ja01525a060 .

[:Wang-2] Z. Wang: Comprehensive organic name reactions and reagents Volume 1 . John Wiley, Hoboken (NJ) 2009, ISBN 978-0-470-28662-3 , pp. 606-610 .