A novel bridged ferrocene derivative

Abramovitch, R. A.; Azogu, C.I.; Sutherland, R. G.

doi:10.1039/c29690001439

Cited by 19 publications

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“…The configuration of the cyclopentadienyl rings is intermediate between the eclipsed and staggered extremes. The angle made by the normals to the planes defined by N-S-C10 and S-N-C5 is 29°; this is in agreement with the value of 25°f ound for the equivalent angle in 6,6,7,7-tetramethyl [2]ferrocenophane. The nature of the configuration is also illustrated by the data in Table IV: for example, the C1-C10 distance is 3.17 A, while the C4-C10 separation is 3.35 A.…”

Section: 70(1)supporting

confidence: 86%

“…This agrees with the 157°value17 given for 6,6,7,7-tetramethyl [2] ferrocenophane, a molecule with a two-atom bridge, and is appreciably smaller than the values for the threeatom-bridged 6-keto [3]ferrocenophane (171°)4 and its 10methyl-8-phenyl derivative (170°).18…”

Section: 70(1)supporting

confidence: 85%

“…Photolysis of ferrocenesulfonyl azide (I) in hydrocarbon so2n3 solvents using 3500-Á radiation yielded [2]ferrocenophanethiazine 1,1-dioxide (II) in good yield.2 The structure of II was established on the basis of its microanalysis and spectral properties. In particular, the NMR spectrum exhibited two sets of A2B2 patterns associated with the two monosubstituted cyclopentadienyl rings, as did the N-methylated product.…”

Section: Introduction Table I Crystal Datamentioning

confidence: 99%

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Crystal structure and Moessbauer spectrum of [2]-ferrocenophanethiazine 1,1-dioxide

Abramovitch¹,

Atwood²,

Good³

et al. 1975

Inorg. Chem.

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Section: 70(1)supporting

confidence: 86%

Section: 70(1)supporting

confidence: 85%

Section: Introduction Table I Crystal Datamentioning

confidence: 99%

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Crystal structure and Moessbauer spectrum of [2]-ferrocenophanethiazine 1,1-dioxide

Abramovitch¹,

Atwood²,

Good³

et al. 1975

Inorg. Chem.

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“…The thermal and photochemical decomposition of ferrocenylsulfonyl azide (1) has led to some very interesting results. 1,2 Thermolysis in benzene led to a unusually high yield (for such reactions3) of hydrogen-abstraction product, ferrocenesulfonamide (2), and to a low yield of "substitution"4 into the aromatic nucleus (3).2 More solvent insertion and less hydrogen abstraction were observed in cyclohexane, but the yield of 2 was very high in cyclohexene. Photolysis of 1 led to quite different results.…”

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confidence: 99%

Ferrocene-1,1'disulfonyl azide and 2,4,6-trimethylpyridinium ferrocenesulfonyl ylide. Synthesis and decomposition

Abramovitch¹,

Holcomb²

1976

J. Org. Chem.

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the end point was not distinct. The products were stored (frozen) in serum bottles under argon. Preparation of 3-Aryl-5,5-dimethylthiazolidine-2-thione~(6a-c). The general method5 was to reflux a mixture of the thiol (3.0 mmol) or disulfide (1.5 mmol), 10 N NaOH (0.30 ml), CSz (7 mmol), and ethanol (10 ml) for 24 hr (argon), add water (3-4 ml), and chill. The crystalline derivative was filtered, waehed (cold MeOH, then H20), and recrystallized from the same ethanolwater mixture prior to analysis. The yields listed are for the crude products. Use of the disulfides 3a and 3c led to similar (or higher) yields of the identical 6 (melting point and mixture melting point). 3-Phenyl-5,5-dimethylthiazolidine-2-thione (sa): colorless plates (45%), mp 114-115'. Anal. Calcd for CllHnNSZ: c , 59.15; H, 5.86; N, 6.27. Found: C, 58.80; H, 5.87; N, 6.17. 3-(p-Chlorophenyl)-5,5-dimethylthiazolidine-2-thione (6b): colorless needles (34%), mp 111-111.5°. Anal. Calcd for C11H12ClNS2: C, 51.25; H, 4.69; N, 5.43. Found: C, 51.34; H, 4.81; N, 5.81. 3 4 p-Dimethylaminophenyl)-5,5-dimethylthiazolidine-2thione (6c): pale yellow needles (79%), mp 156-157O (lit5 157-158O). Nickel(I1) Complex of 5. A solution of 5 (1 mmol) in MeOH (4 ml) was added to a warm solution of Ni(OAc)~.4H20 (1 mmol) in MeOH (8 ml). The solid, which separated immediately, was filtered, washed (MeOH), and vacuum dried (1 hr at 50') to give 188 mg (61.4%) of the tan-pink crystalline complex. Its ir spectrum exhibited bands a t 3220 and 3270 cm-l (sh) (coordinated NH). Anal. Calcd for CloHZ2N2SzNi.%H20: C, 39.75; H, 7.67; N, 9.27. Found: C, 39.67; H, 7.85; N, 9.59. Registry No.-la, No attempt was made to optimize yields. (17) We have no explanation as yet for the uptake of less l2 by those thiols containing aliphatic amino groups.Photolysis of ferrocene-1,l'-disulfonyl azide in various solvents and a t different wavelengths gave 1'-sulfamylferrocenesulfonyl azide and ferrocene-1,l'-disulfonamide. The thermolysis products depended on the solvent used. In cyclohexane, 1'-sulfamylferrocenesulfonyl azide, ferrocene-1,l'-disulfonyl azide, N,N'dicyclohexylferrocene-1,l'-disulfonamide, 1'-(N-cyclohexylsulfamy1)ferrocenesulfonyl azide, and 1'-(N-cyclohexylsulfamy1)ferrocenesulfonamide were obtained. In benzene, products both of kinetic (azepine) and thermodynamic control (anilide) were formed but disubstitution did not occur. In mesitylene, the dimesitylamide was obtained. No intramolecular cyclization products were ever detected. 2,4,6-Trimethylpyridinium ferrocenesulfonyl ylide did not undergo photolysis but did thermolyze to ferrocenesulfonamide and sym-collidine. Again no ferrocenophane was formed.

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“…The decomposition of the triethylammonium salt of Np-nitrobenzenesulfonoxybenzenesulfonamide (13) in protic solvents (MeOH, EtOH, PhNH2) gives products derived from a Lossen-type rearrangement. 12 The rearrangement was thought not to involve a free nitrene, since, when the decomposition was carried out in toluene-methylene chloride or in benzene, no sulfonanilides were obtained.…”

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Reaction of methanesulfonyl nitrene with benzene. Attempts to generate sulfonyl nitrenes from sources other than the azides

Abramovitch¹,

Bailey²,

Takaya³

et al. 1974

J. Org. Chem.

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A novel bridged ferrocene derivative

Abstract: The picture is complicated further by the fact that ferrocene is a very efficient triplet quencher as well as a sensitiser.sThe Transition Elements," 3rd edn., Methuen, London, 1968.

Cited by 19 publications

References 0 publications

Crystal structure and Moessbauer spectrum of [2]-ferrocenophanethiazine 1,1-dioxide

Crystal structure and Moessbauer spectrum of [2]-ferrocenophanethiazine 1,1-dioxide

Ferrocene-1,1'disulfonyl azide and 2,4,6-trimethylpyridinium ferrocenesulfonyl ylide. Synthesis and decomposition

Reaction of methanesulfonyl nitrene with benzene. Attempts to generate sulfonyl nitrenes from sources other than the azides

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