2012
DOI: 10.1021/om300563n
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First Annelated Azaphosphole-Ferrocenes: Synthetic Pathways and Structures

Abstract: The first annelated bis-and mono-3H-1,3azaphosphole ferrocene sandwich compounds have been synthesized from aminoferrocenes, and their X-ray structures are compared to those of their selenide-protected PSe analogues, showing net discrepancies both in metallocene backbone conformation and in fused-ring planarity.

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Cited by 18 publications
(15 citation statements)
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“…The synthetic sequence (Scheme ) follows the route developed for the stable neopentyl‐substituted congener. It starts from readily available 1,1′‐diaminoferrocene,20 used as such or alternatively liberated in situ from its air‐stable hydrochloride20a,20c with potassium carbonate. This diamine was subjected to a condensation reaction with p ‐(dimethylamino)benzaldehyde or p ‐methoxybenzaldehyde to afford the diiminoferrocene derivatives [fc(N=CH‐ p ‐C 6 H 4 ‐NMe 2 ) 2 ] ( 1a ) and [fc(N=CH‐ p ‐C 6 H 4 ‐OMe) 2 ] ( 1b ), respectively.…”
Section: Resultsmentioning
confidence: 99%
“…The synthetic sequence (Scheme ) follows the route developed for the stable neopentyl‐substituted congener. It starts from readily available 1,1′‐diaminoferrocene,20 used as such or alternatively liberated in situ from its air‐stable hydrochloride20a,20c with potassium carbonate. This diamine was subjected to a condensation reaction with p ‐(dimethylamino)benzaldehyde or p ‐methoxybenzaldehyde to afford the diiminoferrocene derivatives [fc(N=CH‐ p ‐C 6 H 4 ‐NMe 2 ) 2 ] ( 1a ) and [fc(N=CH‐ p ‐C 6 H 4 ‐OMe) 2 ] ( 1b ), respectively.…”
Section: Resultsmentioning
confidence: 99%
“…Together with structural information provided by X-ray diffraction studies, a suite of 2D NMR experiments verify the identity and location of the atoms involved in this coupling (Figures S1–S4). Through-space 13 C– 31 P coupling is rarely observed; however, the relatively close proximity of the phosphido ligand P atom to the NHC ligand mesityl methyl C atom (∼3.8 Å) combined with the pyramidalization at P (∑∠ ≈ 340°) and the orientation of the P atom lone pair toward the C atom equip 1 for this spin–spin interaction.…”
mentioning
confidence: 99%
“…Compounds V and VI are examples of related annulated conjugated ring systems 19. Recently, examples have also appeared with ring annulation to ferrocene 20…”
Section: Introductionmentioning
confidence: 99%