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  • 1
    Electronic Resource
    Electronic Resource
    Organische Synthesen mit Übergangsmetall-Komplexen, 64[1]. 1,4-Diaminonaphthaline über Ketenimin-Komplexe aus (β-Aminovinylcarben)chrom-Komplexen und Isocyaniden (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 1867-1872 
    Details
    ISSN: 0009-2940
    Keywords: Aminobenzannulation with isocyanides ; 1,4-Diaminonaphthalines ; Alkynylcarbene complexes ; β-Aminovinylcarbene complexes ; Dienylketenimine complexes ; 4-Amino-1-chroma-1,3-dienes ; Chromium complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Organic Syntheses via Transition Metal Complexes, 64[1]. - 1,4-Diaminonaphthalines via Ketenimine Complexes from (β-Aminovinylcarbene)chromium Complexes and IsocyanidesThe thermal reaction of (dienylcarbene)chromium complexes (= 1-chroma-1,3,5-trienes) with isocyanides provides a mild and regiospecific access to aromatic amines. Thus, 1,4-diamino-2-ethoxynaphthalines 6a-d [1-NHc-C6H11; 4-NRR1 = NMe2 (a) (S)-2-hydroxymethylpyrrolidinyl (b) (1R,2S)-2-methylamino-1-phenyl-1-propanol (c), NtBuMe (d)] are obtained by the cyclization of (E)-(β-aminostyrylcarbene)chromium complexes (CO)5Cr=C(OEt)CH=C(NRR1)C6H5 [(E)-3a-d] with cyclohexyl isocyanide (4) at 90°C in 72-85%. The aminocarbene complexes (E)-3a-d are accessible with high stereoselectivity [〉95% (E) configuration] and chemical yields of 91-96% by the addition of secondary amines HNRR1 2a-d to the (1-alkoxy-3-phenylpropynylidene)chromium complex (CO)5Cr=C(OEt)C≡CC6H5 (1). 3 and 4 give initially mono- and bis(isocyanide) complexes, e.g. (E)-8a and (E)-9a, and subsequently dienylketenimine complexes by the insertion of 4 into the M=C bond of 3. Dienylketenimine complexes are key intermediates in the formation of 6.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260818
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  • 2
    Electronic Resource
    Electronic Resource
    Organische Synthesen mit Übergangsmetallkomplexen, 70. [2-(Galactopyranosylamino)ethenyl]carben- und 3-(Galactopyranosylamino)-1,2-propadienyliden-Komplexe durch 3-Addition von 2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosylamin an Alkinylcarben-Komplexe (M = Cr, W).  -  Atropisomere Galactopyranosyl-Pyrrole durch Reaktion von [2-(Galactopyranosylamino)ethenyl]carben-Komplexen mit Isocyaniden (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 725-729 
    Details
    ISSN: 0009-2940
    Keywords: [2-(Amino)ethenyl]carbene complexes ; 3-Amino-1,2-propadienylidene complexes ; (2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosylamine, carbene complexes of ; Ketene imines ; Isocyanides ; Pyrroles ; Alkynylcarbene complexes of chromium and tungsten ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Organic Syntheses via Transition Metal Complexes, 70[1].  -  [2-(Galactopyranosylamino)ethenyl]carbene and 3-(Galactopyranosylamino)-1,2-propadienylidene Complexes on 3-Addition of 2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosylamine to Alkynylcarbene Complexes (M = Cr, W).  -  Atropisomeric Galactopyranosyl Pyrroles by Reaction of [2-(Galactopyranosyl-amino)ethenyl]carbene Complexes with IsocyanidesEnantiomeric pure (2-aminoethenyl)carbene complexes LnM=C(OEt)—CH=C(Ph)NHR* (Z)-3 and 3-amino-1,2-propadienylidene complexes LnM=C=C=C(Ph)NHR* 4 [R* = 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl] are obtained by the addition of galactopyranosylamine R*-NH2 2 to the corresponding alkynylcarbene complexes LnM=C(OEt)—C≡CPh 1 [LnM = (CO)5Cr, (CO)5W]. Treatment of (Z)-3 with two equivalents of tert-butyl isocyanide (5) affords isocyanide complexes 6 and ketene imines 7. The latter cyclize spontaneously to give galactopyranosylpyrroles 8 which form stable atropisomers 8A and 8B.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270423
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  • 3
    Electronic Resource
    Electronic Resource
    Organic Syntheses via Transition Metal Complexes, 74[1] Novel Phosphonium Allenide and 2-Phosphanylethenyl Carbene Chromium and Tungsten Complexes (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 2475-2482 
    Details
    ISSN: 0009-2940
    Keywords: Vinylcarbene complexes ; Chromium complexes ; Tungsten complexes ; Phosphorus ylide complexes ; Alkynylcarbene complexes ; Allene complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Alkynylcarbene complexes (CO)5M≡C(OEt)-C≡C—R 1 (M = Cr, W; R = Ph, tBu, SiMe3) readily add tertiary phosphanes PPhR2′ 4 (R′ = Ph, Me) to form stable zwitterionic phosphonium allenide complexes (CO)5M--C(OEt) = C≡C(R)-P+PhR2′ 5. Complex 5a (M = Cr, R = R′ = Ph) was characterized by X-ray diffraction. The addition of secondary phosphanes PHR2 6 to 1 affords red (2-phosphanyl ethenyl)-carbene complexes (CO)5M≡C(OEt)-CH≡C(R)-PR2 (E)-8 (R = tBu, cC6H11, Ph) in 34-89% isolated yields. Dinuclear complexes (CO)5M≡C(OEt)-CH≡C(R)-P(R2)M(CO)5 (E)-9 are obtained as byproducts. Compounds (E)-8b (M = Cr, R = cC6H11) and (E)-9i (M = Cr, R = Ph) were characterized by X-ray analyses.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941271218
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  • 4
    Electronic Resource
    Electronic Resource
    Ketenimine Complexes from Carbene Complexes and Isocyanides: Versatile Building Blocks for Carbocycles and N-Heterocycles [New Synthetic Methods (74)]Dedicated to Professor Ernst Otto Fischer on the occasion of his 70th birthday (1988)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 27 (1988), S. 1456-1467 
    Details
    ISSN: 0570-0833
    Keywords: Ketenimines ; Carbene ligands ; Isocyanides ; Carbocycles ; Heterocycles ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ketenimine complexes are readily available in great variety by reaction of isocyanides with carbene complexes. They have proven to be useful building blocks in new synthetic approaches to carbocyclic and N-heterocyclic four-, five-, and six-membered rings. The reactions involve new metal-induced bond formation patterns of the ketenimine ligands, which can be influenced across a wide range by varying the following five parameters: the metal, the ligands, and the three substituents on the N=C=C unit.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198814561
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