Synthetic, structural and electrochemical studieson some ferrocenylazines: crystal structuresof [4]( 1)( 1,4-dimethyl-2,3-diazabuta- 1,3-dien) ferrocenophaneand [42 ](1,1') bis( 1,4-dimethyl-2,3-diazabuta- 1,3-dien) ferrocenophane

AG Osborne, Mateus Webba da Silva, MB Hursthouse, KMA Malik, G Opromolla, P Zanello

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Abstract

By reaction of the hydrazones of mono- and 1,1'-diacetylferrocene with mono- and diketones a series of ferrocenylazines has beenprepared. The crystal structures of the monobridged ferrocenophane [4](1)(1,4-dimethyl-2,3-diazabuta-1,3-dien) ferrocenophane (II) andof the dibridged ferrocenophane [42 ](1, l')bis-(1,4-dimethyl-2,3-diazabuta-1,3-dien) ferrocenophane (VII) have been determined. II existsas a centrosymmetric molecule with eclipsed cyclopentadienyl rings and a planar MeC=NN=CMe bridge whereas VII has staggeredcyclopentadienyl rings and non-planar bridges. In II and VII the bridges are in the E,E configuration. The electrochemical results showthat the ferrocenium ions of the acetylferrocene and the azines are stable in solution whereas those of the hydrazones are unstable. Inagreement with a slightly increasing electronic communication between the two ferrocene units, II undergoes two almost overlappingone-electron oxidations (AE °' = 0.09 V) whereas VII displays two more widely separated one-electron oxidations (AE °' = 0.12 V).
LanguageEnglish
Pages167-176
JournalJournal of Organometallic Chemistry
Volume516
Publication statusPublished - 1996

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Hydrazones
Crystals
Oxidation
Electrons
Crystal structure
Ions
Molecules
Communication
ferrocenium
ferrocene
1-acetylferrocene

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@article{f603f951793a4e4991d2c4f098ee06d5,
title = "Synthetic, structural and electrochemical studieson some ferrocenylazines: crystal structuresof [4]( 1)( 1,4-dimethyl-2,3-diazabuta- 1,3-dien) ferrocenophaneand [42 ](1,1') bis( 1,4-dimethyl-2,3-diazabuta- 1,3-dien) ferrocenophane",
abstract = "By reaction of the hydrazones of mono- and 1,1'-diacetylferrocene with mono- and diketones a series of ferrocenylazines has beenprepared. The crystal structures of the monobridged ferrocenophane [4](1)(1,4-dimethyl-2,3-diazabuta-1,3-dien) ferrocenophane (II) andof the dibridged ferrocenophane [42 ](1, l')bis-(1,4-dimethyl-2,3-diazabuta-1,3-dien) ferrocenophane (VII) have been determined. II existsas a centrosymmetric molecule with eclipsed cyclopentadienyl rings and a planar MeC=NN=CMe bridge whereas VII has staggeredcyclopentadienyl rings and non-planar bridges. In II and VII the bridges are in the E,E configuration. The electrochemical results showthat the ferrocenium ions of the acetylferrocene and the azines are stable in solution whereas those of the hydrazones are unstable. Inagreement with a slightly increasing electronic communication between the two ferrocene units, II undergoes two almost overlappingone-electron oxidations (AE °' = 0.09 V) whereas VII displays two more widely separated one-electron oxidations (AE °' = 0.12 V).",
author = "AG Osborne and {Webba da Silva}, Mateus and MB Hursthouse and KMA Malik and G Opromolla and P Zanello",
year = "1996",
language = "English",
volume = "516",
pages = "167--176",

}

TY - JOUR

T1 - Synthetic, structural and electrochemical studieson some ferrocenylazines: crystal structuresof [4]( 1)( 1,4-dimethyl-2,3-diazabuta- 1,3-dien) ferrocenophaneand [42 ](1,1') bis( 1,4-dimethyl-2,3-diazabuta- 1,3-dien) ferrocenophane

AU - Osborne, AG

AU - Webba da Silva, Mateus

AU - Hursthouse, MB

AU - Malik, KMA

AU - Opromolla, G

AU - Zanello, P

PY - 1996

Y1 - 1996

N2 - By reaction of the hydrazones of mono- and 1,1'-diacetylferrocene with mono- and diketones a series of ferrocenylazines has beenprepared. The crystal structures of the monobridged ferrocenophane [4](1)(1,4-dimethyl-2,3-diazabuta-1,3-dien) ferrocenophane (II) andof the dibridged ferrocenophane [42 ](1, l')bis-(1,4-dimethyl-2,3-diazabuta-1,3-dien) ferrocenophane (VII) have been determined. II existsas a centrosymmetric molecule with eclipsed cyclopentadienyl rings and a planar MeC=NN=CMe bridge whereas VII has staggeredcyclopentadienyl rings and non-planar bridges. In II and VII the bridges are in the E,E configuration. The electrochemical results showthat the ferrocenium ions of the acetylferrocene and the azines are stable in solution whereas those of the hydrazones are unstable. Inagreement with a slightly increasing electronic communication between the two ferrocene units, II undergoes two almost overlappingone-electron oxidations (AE °' = 0.09 V) whereas VII displays two more widely separated one-electron oxidations (AE °' = 0.12 V).

AB - By reaction of the hydrazones of mono- and 1,1'-diacetylferrocene with mono- and diketones a series of ferrocenylazines has beenprepared. The crystal structures of the monobridged ferrocenophane [4](1)(1,4-dimethyl-2,3-diazabuta-1,3-dien) ferrocenophane (II) andof the dibridged ferrocenophane [42 ](1, l')bis-(1,4-dimethyl-2,3-diazabuta-1,3-dien) ferrocenophane (VII) have been determined. II existsas a centrosymmetric molecule with eclipsed cyclopentadienyl rings and a planar MeC=NN=CMe bridge whereas VII has staggeredcyclopentadienyl rings and non-planar bridges. In II and VII the bridges are in the E,E configuration. The electrochemical results showthat the ferrocenium ions of the acetylferrocene and the azines are stable in solution whereas those of the hydrazones are unstable. Inagreement with a slightly increasing electronic communication between the two ferrocene units, II undergoes two almost overlappingone-electron oxidations (AE °' = 0.09 V) whereas VII displays two more widely separated one-electron oxidations (AE °' = 0.12 V).

M3 - Article

VL - 516

SP - 167

EP - 176

ER -