The 'inverse electron-demand' Diels-Alder reaction in polymer synthesis. Part 4.1 the preparation and crystal structures of some bis(1,2,4,5-tetrazines)

Christopher Glidewell, Philip Lightfoot, Brodyck J.L. Royles, David M. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

Reaction of 3,6-bis(3,5-dimethylpyrazolyl)-1,2,4,5-tetrazine with mono- and di-amines gives rise to nucleophilic substitution of one or both of the pyrazolyl substituents, and reaction with diamines under appropriate conditions can lead to bis(3-amino-1,2,4,5-tetrazines), e.g. 12a, 12b and 13. The crystal structures of two of these (12a and 13) show electronic interaction between the tetrazine rings and the amino groups, but none between the tetrazine and pyrazole rings. In 12a there is an extensive network of N-H ⋯ N hydrogen bonds.

Original languageEnglish
Pages (from-to)1167-1174
Number of pages8
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number6
DOIs
Publication statusPublished - 1 Jan 1997

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