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  • General Chemistry  (12)
  • Arsaalkenes  (3)
  • 1,3-Cyclopentadiene-5-carbonyl chloride, 1,2,3,4,5-pentamethyl-  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Bis(pentamethylcyclopentadienyl)keton und -thioketon: Kohlenstoff-Verbindungen mit präformierter Diels-Alder-Geometrie (1993)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 415-420 
    Details
    ISSN: 0009-2940
    Keywords: 1,3-Cyclopentadiene-5-carbonyl chloride, 1,2,3,4,5-pentamethyl- ; 1,3-Cyclopentadiene-5-carbothioyl chloride, 1,2,3,4,5-pentamethyl- ; Ketone, bis(1,2,3,4,5-pentamethyl-1,3-cyclopentadien-5-yl) ; Thioketone, bis(1,2,3,4,5-pentamethyl-1,3-cyclopentadien-5-yl) ; Diels-Alder preformation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bis(pentamethylcyclopentadienyl) Ketone and Thioketone: Carbon Compounds with Performed Diels-Alder Geometry1,2,3,4,5-Pentamethyl-1,3-cyclopentadien-5-carbonyl chloride (2) is formed in good yields by the reaction of pentamethylcyclopentadienyllithium (1) with phosgene. The corresponding carbothioyl chloride 3 is synthesized by treatment of 1 with thiophosgene. Both acyl chlorides are stable against air and moisture and difficult to attack in SN2-type reactions. Treatment of 2 and 3 with trimethyl(pentamethylcyclopentadienyl)stannane in the presence of boron trifluoride  -  ether leads to bis(1,2,3,4,5-pentamethyl-1,3-cyclopentadien-5-yl) ketone (5) and thioketone (6), respectively. Even at room temperature, 5 and 6 tend to intramolecular [4 + 2] cycloaddition reactions. X-ray crystal structure investigations of 2, 5, and 6 show the steric demand of the pentamethylcyclopentadienyl ligand and explain the untypical chemical behavior of 2 and the easy [2 + 4] cycloaddition reactions of 5 and 6.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19931260219
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  • 2
    Electronic Resource
    Electronic Resource
    Transition Metal-Substituted Arsaalkenes, II. Synthesis, Structure and Reactivity of the Arsaalkenes RAs=C(NMe2)2 [R = Me3Si, (η5-C5Me5)(CO)2Fe] and the 1,2-Dihydroarsete (η5-C5Me5)(CO)2-Fe (1996)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 129 (1996), S. 223-226 
    Details
    ISSN: 0009-2940
    Keywords: Arsaalkenes ; Carbonyliron complexes ; Arsete, 1,2-dihydro- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of equimolar amounts of thiuronium salt [(Me2N)2C-SMe]I (1, with LiAs(SiMe3)2 · 2 THF (2) afforded arsaalkene Me3SiAs=C(NMe2)2 (3). Combination of 3 with (η5-C5Me5)(CO)2 FeBr led to the formation of (η5-C5Me5)(CO)2-FeAs=C(NMe2)2 (4). Reaction of the latter with dimethyl fumarate gave the 1,2-dihydroarsete (η5-C5Me5)(CO)2-Fe (6). Compounds 3, 4, and 6 were characterized by means of spectroscopy (IR, 1H, 13C{1H}, 29Si{1H} NMR and mass spectrometry). The molecular structures of 4 and 6 were determined by X-ray diffraction analysis.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19961290217
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  • 3
    Electronic Resource
    Electronic Resource
    Metalloarsaalkene [(η5-C5Me5)(CO)2FeAs=C(NMe2)2] as a Ligand in Carbonylchromium, -iron, and -nickel Complexes (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 55-59 
    Details
    ISSN: 1434-1948
    Keywords: Arsaalkenes ; Arsenic ligands ; Carbonyl complexes ; Chromium ; Iron ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of equimolar amounts of the metalloarsaalkene [(η5-C5Me5)(CO)2FeAs=C(NMe2)2] (1) with the carbonyl complexes [Ni(CO)4], [Fe2(CO)9], and [{(Z)-cyclooctene}Cr(CO)5], respectively, affords the adducts [(η5-C5Me5)(CO)2FeAs{M(CO)n}=C(NMe2)2] with [M(CO)n] = [Ni(CO)3] (2); [Fe(CO)4] (3), and [Cr(CO)5] (4). These feature η1 coordination of the arsaalkene ligand via the arsenic atom. The molecular structures of the complexes 3 and 4 have been determined by X-ray diffraction analyses.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis and Structure of the First Carbyne Complex Functionalized Zwitterionic α-Carbenium Phosphinates [Tp′(CO)2M ≡ C-P(O)2-C(NR2)2] (M = Mo, W; R = Me, Et) (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 579-582 
    Details
    ISSN: 1434-1948
    Keywords: Carbyne complexes ; Molybdenum complexes ; Oxidations ; Tungsten ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oxidation of the phosphaalkenyl-substituted carbyne complexes [Tp′(CO)2M≡C-P=C(NR2)2] (1a: M = Mo, R = Me; 1b: M = W, R = Me; 2a: M = Mo, R = Et; 2b: M = W, R = Et) with molecular dioxygen cleanly affords the orange carbyne complexes [Tp′(CO)2M≡C-P(O)2C(NR2)2] [3a: M = Mo, R = Me; 3b: M = W; R = Me; 4a: M = Mo, R = Et; 4b: M = W, R = Et; Tp′ = HB(3,5-Me2HC3N2)3], which are functionalized at the methylidyne carbon atom by an α-carbenium phosphinate moiety. The novel compounds have been characterized by IR, 1H-, 13C-, and 31P-NMR spectroscopy. In addition, the molecular structure of 4a has been determined by a single-crystal X-ray structure analysis.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Reactivity of Ferriophosphaalkene [(η5-C5Me5)(CO)2Fe-P=C(NMe2)2] and Ferrioarsaalkene [(η5-C5Me5)(CO)2Fe-As=C(NMe2)2] Towards Trimethylaluminium, -gallium and -indium (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 1607-1611 
    Details
    ISSN: 1434-1948
    Keywords: Arsaalkenes ; Phosphaalkenes ; Aluminium ; Gallium ; Indium ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of equimolar amounts of the ferriophosphaalkene [(η5-C5Me5)(CO)2FeP=C(NMe2)2] (1a) or the ferrioarsaalkene [(η5-C5Me5)(CO)2FeAs=C(NMe2)2] (1b) with trimethylaluminium, trimethylgallium and trimethylindium afforded the adducts [(η5-C5Me5)(CO)2FeE{MMe3}C(NMe2)2] with E = P; M = Al (2a), Ga (3a), In (4a) and E = As; M = Al (2b), Ga (3b), and In (4b). These compounds feature η1-coordination of the phosphaalkene or the arsaalkene ligand towards the Lewis acid via the pnictogen atom. The molecular structures of 2a and 3a were elucidated by X-ray diffraction analyses.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis and Structure of 2-Hydro-, 2-Alkyl-, 2-Alkynyl-, and 2-Stannyl-2,3-dihydro-1H-1,3,2-diazaboroles (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 491-497 
    Details
    ISSN: 1434-1948
    Keywords: Boron ; Diazaboroles ; Hydrides ; Tin ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,3-Di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaborole (4a) and 1,3-bis(2,6-dimethylphenyl)-2,3-dihydro-1H-1,3,2-diazaborole (4b) were formed by the reaction of the corresponding 2-bromo or 2-iodo derivatives 1a and 2b with LiAlH4. Treatment of 1a with n-butyllithium afforded 2-n-butyl-1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaborole (5a), whereas 1,3-di-tert-butyl-2-cyano-2,3-dihydro-1H-1,3,2-diazaborole (3a) was converted into the 2-tert-butyl derivative 6a or the 2-ethynyl-1,3,2-diazaborole 7a by means of tert-butyllithium or by the ethylenediamine adduct of lithium acetylide. Similarly, 1,3-di-tert-butyl-2-trimethylstannyl-2,3-dihydro-1H-1,3,2-diazaborole (8a) and 1,3-bis(2,6-dimethylphenyl)-2-trimethylstannyl-2,3-dihydro-1H-1,3,2-diazaborole (8b) were accessible from 1a or 2b and trimethylstannyllithium. In the complex 9a the compound 3a serves as an η1 ligand towards the [Cr(CO)5] unit via the cyano group. These novel compounds were characterized by 1H-, 11B-, 13C-, and 119Sn-NMR spectroscopy, as well as by X-ray structure analyses of 4b, 8a, and 9a.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Terpyridines Functionalised with Ferrocenyl Groups of Different Redox Potential (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 1-5 
    Details
    ISSN: 1434-1948
    Keywords: Terpyridine ligands ; Ferrocenes ; Iron ; Ruthenium ; Cyclic voltammetry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,2′:6′,2′′-Terpyridines bearing a substituent × in the 4′-position [3a: × = Fc-C≡C-p-C6H4; 3b: × = Fc#-C≡C-p-C6H4; Fc = (C5H5)Fe(C5H4), Fc# = (C5Me4H)Fe(C5Me4)] were prepared by Pd0-catalysed cross-coupling reactions. 3b was characterised by X-ray structure analysis. [(3a)RuCl2(DMSO)] (4a) and [(3b)RuCl2(DMSO)] (4b) were obtained by reaction of [RuCl2(DMSO)4] with 1 equivalent of 3a and 3b, respectively, while the analogous reaction with 2 equivalents afforded [(3a)2Ru][PF6]2 (5a) and [(3b)2Ru][PF6]2 (5b), respectively, after precipitation with aqueous [NH4][PF6]. Similarly, [(3a)Ru(tpy)][PF6]2 (6) was isolated from the reaction of 4a with 2,2′:6′,2′′-terpyridine (tpy). Compounds 3 and 5 were investigated by cyclic voltammetry, which revealed that the introduction of eight methyl groups leads to the expected cathodic shift of the E0′ values of ca. 0.44 V for the ferrocenyl-centered redox processes.
    Additional Material: 1 Ill.
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  • 8
    Electronic Resource
    Electronic Resource
    Reactivity of Carbonyl-Functionalized Phosphaalkenes RC(O)P=C(NMe2)2 (R = tBu, Ph) towards Electrophiles (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 2369-2381 
    Details
    ISSN: 1434-1948
    Keywords: Alkylation ; Carbonyl complexes ; Lewis acids ; Phosphaalkenes ; Protonation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of the carbonyl-functionalized phosphaalkenes RC(O)P=C(NMe2)2 [R = tBu (2a), Ph (2b)] with protic acids and alkylating reagents occurred at the two-coordinate phosphorus atom to give the phosphanyl-substituted carbocations 3a,b and 4a,b. In contrast, treatment with Me3SiOSO2CF3 resulted in attack at the oxygen atom by the silyl group, and the formation of [RC(OSiMe3)=PC(NMe2)2]SO3CF3 (5a,b). Similarly, the Lewis acids B(C6F5)3, Al(tBu)2Cl and AlMe3 were ligated to the oxygen atom of the carbonyl group. Two equivalents of GaMe3 were added to the oxygen and phosphorus atom of the phosphaalkene to yield the thermolabile complexes [RC(OGaMe3)=P(GaMe3)C(NMe2)2] (10a,b). In contrast, one molecule of InMe3 was bound to the phosphorus center of the phosphorus compound. Reaction of the phosphaalkenes with [Ni(CO)4], [Fe2(CO)9] or [{(Z)-cyclooctene}Cr(CO)5] also took place at the pnictogen atom, resulting in complexes of the type [RC(O)P{M(CO)n}C(NMe2)2] (R = tBu, Ph; M = Ni, n = 3; Fe, n = 4; Cr, n = 5). The chemical transformations reported here underline the versatile chemistry of phosphaalkenes and emphasize a relationship between carbonyl-functionalized phosphaalkenes and the well-investigated class of phosphorus ylides. X-ray structures of compounds 6b, 7b*, 10a, 11a and 12a are reported.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis, Structure and Reactivity of 3,4-Dihydro-2H-1,2,4,3-triazaboroles (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 1193-1198 
    Details
    ISSN: 1434-1948
    Keywords: Boron ; Triazaboroles ; Heterocycles ; Halogens ; Cyanides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 3,4-Dihydro-2,4-diphenyl-2H-1,2,4,3-triazaboroles 3a, 3b, and 4 were synthesized by cyclocondensation of N1,N3-diphenylformamidrazone (1) with dibromophenylborane, dibromomethylborane, and boron trichloride. 3-Chloro-3,4-dihydro-2,4-diphenyl-2H-1,2,4,3-triazaborole (4) was converted into 3,4-dihydro-2,4-diphenyl-2H-1,2,4,3-triazaborole (5) by treatment with LiAlH4. The corresponding 3-cyanato and 3-cyano derivatives 6 and 7 resulted from the reaction of 4 with AgOCN and AgCN, respectively. Compound 7 was transformed into the bis(1,2,4,3-triazaborolyl)oxane 8 by silver oxide. Compounds 1-8 were characterized by elemental analyses and spectroscopic methods (1H, 11B, and 13C NMR; IR; MS). The molecular structure of 8 was established by single-crystal X-ray diffraction analysis.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    A Tandem Hexaannulation Reaction of Benzyllithium Involving Base-Induced Cyclodehydrogenation (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2879-2884 
    Details
    ISSN: 1434-193X
    Keywords: Metallation ; Elimination reactions ; Cyclization ; Cyclodehydrogenation ; Polycyclic hydrocarbons ; Propellanes ; Strained olefins ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of the tribenzo[3.3.3]propellane ketone 1 (triptindan-9-one) with benzyllithium/TMEDA affords an efficient one-pot peri annulation of a dihydronaphthalene across two wings of the propellane framework. The key step of this surprising tandem reaction was determined to be a nucleophilic cyclization of (Z)-9-benzylidenetriptindane (4) with concomitant hydride elimination. The formation of the novel centrotetracyclo[5.5.5.6] framework bearing a distorted (E)-stilbene unit was confirmed by single-crystal X-ray structure analysis.
    Additional Material: 1 Ill.
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