The first 1,3,2-diazaphospha-[3]ferrocenophanes

Wrackmeyer, Bernd; Klimkina, Elena V.; Milius, Wolfgang

doi:10.1016/j.inoche.2004.04.026

Cited by 18 publications

(23 citation statements)

References 28 publications

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“…The synthesis of 4a, c, d (Scheme 2) followed the conventional method reported for 2a -2d [13], whereas 4b was prepared by using the phenoxyphosphoryl dichloride by an analogous procedure as described for 4a. These bulky aminophosphanes are of low reactivity, except for hydrolysis, since the reaction of neither 2a (Et 2 O, 4 d, r. t.) nor 4a (toluene, 20 h at r. t., 1 h at 70…”

Section: Synthesismentioning

confidence: 99%

“…Thus, aminophosphanes as P(III) compounds as well as the corresponding P(V) compounds are well studied in many respects, including their molecular structures [2] and numerous NMR properties [3]. Cyclic P-N compounds are of interest with respect to their conformation and molecular dynamics which are most efficiently studied by NMR spectroscopy, mostly by 1 H, 13 C and 31 P NMR [3 -6]. In the case of cyclic Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

“…In the case of cyclic Scheme 1. 1,1 -Diaminoferrocene [11,12] and four 1,3, 2-diazaphospha [3]ferrocenophanes reported in a preliminary study [13].…”

Section: Introductionmentioning

confidence: 99%

“…In a preliminary report [13], we have disclosed the synthesis and molecular structures of 2a and 2d, and it was pointed out that the 2-phenyl derivative 3a may have a different structure as far as the mutual orientation of the P-C and the N-H bonds Table 1. 13 C, 31 P, 77 Se and 1 H NMR data a,b of the 2-phenoxy-1,3,2-diazaphospha- [3] are concerned. To the best of our knowledge, there are no fully characterized cyclic diaminophosphanes which differ in their principal conformation owing to effects exerted by substituents at the phosphorus atom.…”

Section: Introductionmentioning

confidence: 99%

“…These properties might be of interest in further studies of such aminophosphanes as ligands in transition metal chemistry. The question of alternative structures raised previously [13] is addressed here in more detail, including the 2-phenoxy group, by using multinuclear 1D and 2D magnetic resonance techniques, and by taking advantage of the results of X-ray structural analysis for two further examples, in addition to those already reported [13] for 2a and 2d.…”

Section: Introductionmentioning

confidence: 99%

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1,3,2-Diazaphospha-[3]ferrocenophanes. Molecular Structures and Multinuclear Magnetic Resonance Studies

Wrackmeyer

Klimkina

Milius

2009

Zeitschrift Für Naturforschung B

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Dedicated to Professor Hubert Schmidbaur on the occasion of his 75 th birthday2-Phenoxy-1,3,2-diazaphospha-[3]ferrocenophane and related derivatives (oxide, sulfide, selenide) were prepared, characterized in solution by multinuclear magnetic resonance methods (1D and 2D 1 H, 13 C, 15 N and 31 P NMR) and in the solid state by X-ray structural analysis. The conformation of the 2-phenoxy derivative differs from that of the 2-tert-butyl compound. For further comparison, 2-R-2,3-dihydro-1H-1,3,2-diazaphospha-phenalene derivatives R = t Bu, PhO were prepared and studied by the same NMR techniques. The molecular structure of a selenide was determined, and together with the NMR evidence, it was concluded that the conformation of these heterocycles is independent of the respective substituent at the phosphorus atom.

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Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…In the case of cyclic Scheme 1. 1,1 -Diaminoferrocene [11,12] and four 1,3, 2-diazaphospha [3]ferrocenophanes reported in a preliminary study [13].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1,3,2-Diazaphospha-[3]ferrocenophanes. Molecular Structures and Multinuclear Magnetic Resonance Studies

Wrackmeyer

Klimkina

Milius

2009

Zeitschrift Für Naturforschung B

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Effects of Structural Factors on the π-Dimerization and/or Disproportionation of the Cation Radical of Extended TTF Containing Thiophene-Based π-Conjugated Spacers

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Ferrocenes Bearing Sulfinylamino Groups

et al. 2006

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1,1′‐Diaminoferrocene (2) and 1,1′‐bis(trimethylsilylamino)ferrocene (3) have been converted into sulfinylamines by treatment with thionyl chloride in the presence of triethylamine. In the case of 2 the 1:2 reaction affords 1,1′‐bis(sulfinylamino)ferrocene (5) and the 1:1 reaction gives 6‐amino‐1‐sulfinylaminoferrocene (6). Bis(trimethylsilylamino)ferrocene reacts with thionyl chloride in a 1:1 molar ratio to give 1‐sulfinylamino‐6‐(trimethylsilylamino)ferrocene (8). In contrast, the reaction of N,N′‐dilithiobis(trimethylsilylamino)ferrocene (4) with thionyl chloride gives the [3]ferrocenophane 9, which contains an N–S(O)–N bridge, rather than sulfinylamines or a sulfur diimide. The molecular structures of 5 and 8 were determined by X‐ray analysis. The 57Fe NMR chemical shift (δ = +2597.0 ppm) for 5 indicates the strong π‐acceptor properties of the NSO groups. Dynamic 1H and 13C NMR spectra prove the hindered rotation of the NSO group about the C–N bonds in 5, 6 and 8. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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The first 1,3,2-diazaphospha-[3]ferrocenophanes

Cited by 18 publications

References 28 publications

1,3,2-Diazaphospha-[3]ferrocenophanes. Molecular Structures and Multinuclear Magnetic Resonance Studies

1,3,2-Diazaphospha-[3]ferrocenophanes. Molecular Structures and Multinuclear Magnetic Resonance Studies

Effects of Structural Factors on the π-Dimerization and/or Disproportionation of the Cation Radical of Extended TTF Containing Thiophene-Based π-Conjugated Spacers

Ferrocenes Bearing Sulfinylamino Groups

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