Synthesis and metallation of ferrocenylimines derived from ligating diaminoheteroarenes

Catherine M. Asselin, Greig C. Fraser, H. K. Hall, W. Edward Lindsell, Anne B. Padias, Peter N. Preston

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Abstract

A regioisomeric mixture of 1,1'-didodecylferrocenedicarbaldehydes 3 was prepared from the reaction of a regioisomeric mixture of 1,1'-didodecyldilithioferrocenes and dimethylformamide. Three ligating heteroaromatics were synthesized each containing two amino substituents: 5,5'-diamino-2,2'-bipyridine and 5,5?-diamino-2,2' : 6',2?-terpyridine were prepared from appropriate dinitro compounds by reduction with palladium on charcoal-hydrazine hydrate. The reaction of 2-cyano-5-nitropyridine and hydrazine hydrate gave an isolable amidine derivative and this was transformed with hydrazine in a separate reaction under more forcing conditions into 3,6-bis(5-amino-2-pyridyl)-1,2-dihydro-1,2,4,5-tetrazine. The latter was converted into the tetrazine by oxidation (2,3-dichlpro-5,6-dicyano-1,4-benzoquinone) and then trifluoroacetylated [(CF3CO)2O] to give the bis(trifluoroacetylamino) derivative. Diels-Alder reaction of the latter with dodec-1-yne afforded 4-n-decyl-3,6-bis[5-(trifluoroacetylamino)-2-pyridyl]pyridazine which was deprotected (K2CO3) to give the corresponding diamine. Bis(ferrocenyl) Schiff bases were prepared from ferrocenecarbaldehyde and the appropriate diamine in either uncatalysed or acid-catalysed condensations. Tetracarbonylmolybdenum complexes were prepared by treating the appropriate diamines with molybdenum hexacarbonyl. Reaction of one of these complexes with ferrocenecarbaldehyde gave a heterobimetallic complex.

Original languageEnglish
Pages (from-to)3765-3771
Number of pages7
JournalJournal of the Chemical Society, Dalton Transactions
Issue number20
Publication statusPublished - 21 Oct 1997

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    Asselin, C. M., Fraser, G. C., Hall, H. K., Lindsell, W. E., Padias, A. B., & Preston, P. N. (1997). Synthesis and metallation of ferrocenylimines derived from ligating diaminoheteroarenes. Journal of the Chemical Society, Dalton Transactions, (20), 3765-3771.