Synthesis and metallation of ferrocenylimines derived from ligating diaminoheteroarenes

被引:15
作者
Asselin, CM [1 ]
Fraser, GC [1 ]
Hall, HK [1 ]
Lindsell, WE [1 ]
Padias, AB [1 ]
Preston, PN [1 ]
机构
[1] UNIV ARIZONA,DEPT CHEM,TUCSON,AZ 85721
来源
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS | 1997年 / 20期
关键词
D O I
10.1039/a703768f
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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-dichloro-5,6-dicyano-1,4-benzoquinone) and then trifluoroacetylated [(CF3CO)(2)O] 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]py 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.
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页码:3765 / 3771
页数:7
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