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  • 1
    Electronic Resource
    Electronic Resource
    Alkali-Phosphorverbindungen und ihr reaktives Verhalten, LI. Synthese und Reaktionsverhalten des [β-Amino-äthyl]-phenyl-phosphins (1967)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 100 (1967), S. 2685-2693 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: NaP(H)C6H5 reagiert in fl. NH3 mit β-Chlor-äthylamin zu [β-Amino-äthyl]-phenyl-phosphin (1). Dessen Oxydation mit Wasserstoffperoxid oder Schwefel liefert [β-Amino-äthyl]-phenyl-phosphinsäure bzw. -dithiophosphinsäure (2, 3). 1 läßt sich in fl. NH3 mit Natrium zu C6H5P(Na)CH2CH2NH2 metallieren, das mit Alkylchloriden tert. (5, 6) bzw. mit α.ω-Dihalogen-alkanen ditert. [β-Amino-äthyl]-phosphine (12-14), mit Epoxiden [β-Aminoäthyl]-[β-hydroxy-alkyl]-phosphine (11) und mit β-Chlor-äthylamin 4-Phenyl-perhydro-1.4-azaphosphorin (9) bildet. Die Kondensation zwischen 1 und Aldehyden bzw. Ketonen führt zu P-phenylsubstituierten 1.3-Azaphospholidinen (18-29).
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19671000832
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  • 2
    Electronic Resource
    Electronic Resource
    Alkali-Phosphorverbindungen und ihr reaktives Verhalten, LIX. Synthese und Reaktionsverhalten der 2-Amino-äthylphosphine (1968)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 101 (1968), S. 3612-3618 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: NaPH2 reagiert in flüss. Ammoniak mit 2-Chlor-äthylaminen zu 2-Amino-äthylphosphinen H2P—CH2—CH2—NRR′(1—3), die als P—H-acide Substanzen nach erneuter Metallierung und Kupplung mit Alkylhalogeniden zu R′′P(H)—CH2—CH2—NRR (4 - 10) und mit Dihalogenalkanen zu [CH2]n(P(H)—CH2—CH2—NR2)2 (13 - 16) führen. Analog lassen sich ausgehend von C6H5PH2 oder 1 und 3 mit 2-Chlor-äthylaminen C6H5P(H)—CH2—CH2—NRR′ und Bis- bzw. Tris-[2-amino-äthyl]-phosphine (17-21) gewinnen. Die Oxydation sek. 2-Aminoäthylphosphine mit Schwefel liefert [2-Amino-äthyl]-alky- bzw. -aryldithiophosphinsäuren (22-26) mit Zwitterionenstruktur. Durch gleichzeitige Einwirkung von Diäthylamin und Formaldehyd auf P—H-funktionelle 2-Amino-äthylphosphine entstehen [(C2H5)2NCH2]nP-[CH2—CH2NR2]3-n (27, 28).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19681011035
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  • 3
    Electronic Resource
    Electronic Resource
    1.3-Azaphospholidine (1968)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 101 (1968), S. 3619-3622 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Amino-äthylphosphine, die sowohl P—H- als auch N—H-Funktionen besitzen, reagieren mit Aldehyden und Ketonen unter cyclisierender Kondensation zu 1.3-Azaphospholidinen (1-2), deren Struktur IR-spektroskopisch sowie nach Umsetzung mit Schwefel als P-Sulfide (13) bzw. Dithiophosphinsäuren (14, 15) mit Betainstruktur bewiesen wurde.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19681011036
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  • 4
    Electronic Resource
    Electronic Resource
    Perhydro-1.3-azaphosphorine (1968)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 101 (1968), S. 4032-4035 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Durch radikalische Addition von Butyl- bzw. Phenylphosphin an Allylamin werden [3-Aminopropyl]-butyl- (1) und [3-Amino-propyl]-phenyl-phosphin (2) erhalten. 1 und 2 reagieren mit Carbonylverbindungen unter cyclisierender Kondensation zu Perhydro-1.3-azaphosphorinen (4 - 9), die durch Umsetzung mit HCl zu entsprechenden Hydrochloriden und durch Oxydation mit Schwefel zu P-Sulfiden charakterisiert werden.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19681011204
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  • 5
    Electronic Resource
    Electronic Resource
    The Acid-Induced Rearrangement of 1-Hydroxyalkyltris(trimethylsilyl)silanes (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 177-181 
    Details
    ISSN: 1434-1948
    Keywords: Silanes ; Rearrangements ; Polysilanes ; Hypersilylalcohols ; 1,2-Trimethylsilyl migration ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In the presence of strong acids, such as HCl or H2SO4, 1-hydroxyalkyltris(trimethylsilyl)silanes (Me3Si)3Si-C(OH)R1R2 (1a-f) isomerize by 1,2-Me3Si/OH exchange to give the trimethylsilylmethylsilanols (Me3Si)2Si(OH)-C(SiMe3)R1R2 (4a-f) [R1,R2: a: Me, Me; b: H, 4-MeC6H4; c: H, 4-iPrC6H4; d: H, Mes; e: H, 2-Me2NC6H4; f: H, 2,4,6-(MeO)3C6H2]. A mechanism for the isomerization is proposed. In the case of the reaction of 1d with sulfuric acid, the silylsulfate (Me3Si)2Si(OSO3H)-C(SiMe3)HMes (5) was isolated. 5 is the intermediate in the H2SO4-catalyzed isomerization of 1d and was converted in situ with methanol, acetic anhydride, HF or HCl to give the respective methoxysilane 6, acetoxysilane 7, fluorosilane 8, or chlorosilane 9. Deprotonation of 4a, d, f with sodium hydride causes a further rearrangement, a 1,3-C,O-trimethylsilyl migration, to give the siloxanes (Me3Si)2(Me3SiO)Si-CHR1R2 (11a, d, f).
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  • 6
    Electronic Resource
    Electronic Resource
    Head-to-Head versus Head-to-Tail Dimerizations of Transient Silenes - The Solvent-Dependent Regiospecifity of the Dimerization of 2-(2-Methoxyphenyl)-1,1-bis(trimethylsilyl)silene (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 1667-1672 
    Details
    ISSN: 1434-1948
    Keywords: Silicon ; Silenes ; 1,2-Disilacyclobutanes ; 1,3-Disilacyclobutanes ; Eliminations ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The regiospecifity of the dimerization of the transient 2-(2-methoxyphenyl)-1,1-bis(trimethylsilyl)silene (6), synthesized by base-initiated trimethylsilanolate elimination from (2-methoxyphenyl)[tris(trimethylsilyl)silyl]methanol (5) according to a modified Peterson mechanism, decisively depends on the donating ability of the solvent in which the silene is generated. In ether, 6 undergoes a formal [2 + 2] dimerization to afford 3,4-bis(2-methoxyphenyl)-1,1,2,2-tetrakis(trimethylsilyl)-1,2-disilacyclobutane (12), whereas in toluene the head-to-tail [2 + 2] cyclodimer, 2,4-bis(2-methoxyphenyl)-1,1,3,3-tetrakis(trimethylsilyl)-1,3-disilacyclobutane (13) was obtained. 1,1-Bis(trimethylsilyl)-2-(2,4,6-trimethoxyphenyl)silene (18), similarly made by a modified Peterson reaction, under the same conditions reacted with the eliminated trimethylsilanolate with readdition at the polar Si=C bond to give, after hydrolysis, 2-(2,4,6-trimethoxybenzyl)-1,1,1,3,3,3-hexamethyl-2-(trimethylsiloxy)trisilane (19). A possible mechanism explaining the solvent-dependent regiospecificity of the dimerization of 6 is discussed. The structures of 12 and 13 were determined on the basis of NMR and MS data as well as X-ray structural analyses.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Geminal Bis(hypersilyl) Compounds - The Reaction of Tris(trimethylsilyl)silyllithium with Dialkyl(chloromethylene)ammonium Chlorides (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 21-26 
    Details
    ISSN: 1434-1948
    Keywords: Silicon ; Silanes, sterically congested ; Tris(trimethylsilyl)silanes ; (Chloromethylene)ammonium chlorides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Tris(trimethylsilyl)silyllithium (1) reacts with dialkyl(chloromethylene)ammonium chlorides (molar ratio 2:1) to give the (dialkylamino)bis(hypersilyl)methanes [(Me3Si)3Si]2CHNR2 (5a-c; a: R = Me, b: R = Et, c: R2 = [CH2]5). Due to the extreme bulkiness of the hemispherical (Me3Si)3Si substituents, the structures of these geminal bis(hypersilyl) derivatives are characterized by tremendous distortions of their molecular skeletons. This was confirmed by X-ray structural analyses of 5a and 5c, which revealed considerable elongations of the central Si-C bonds (5a: 2.01 and 1.95 Å; 5c: 1.99 and 1.97 Å) and an extreme widening of the Si-C-Si angles at the central sp3-carbon atoms (5a: 132.6°; 5c: 128.7°). By concentrated sulfuric acid, 5a is converted to give, after hydrolysis, the silanol (Me3Si)2Si(OH)-CH2Si(SiMe3)3 (13). The formation of 13 is discussed as proceeding through the transient silene (Me3Si)2Si=CHSi(SiMe3)3 (11), generated by a formal (dimethylamino)trimethylsilane elimination from 5a according to an acid-induced sila Peterson mechanism.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Die Bildung und ungewöhnliche Dimerisierung von 2-Mesityl-1,1-bis(trimethylsilyl)silenDiese Arbeit wurde von der Deutschen Forschungsgemeinschaft und dem Fonds der Chemischen Industrie gefördert. (1994)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 106 (1994), S. 1709-1712 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19941061532
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  • 9
    Electronic Resource
    Electronic Resource
    The Synthesis and Dimerization of Transient 1-Silabutadienes (1996)
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 622 (1996), S. 801-806 
    Details
    ISSN: 0044-2313
    Keywords: Silabutadienes ; syntheses ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthese und Dimerisierung instabiler 1-SilabutadieneDurch Umsetzung des Tris(trimethylsilyl)-silyllithiums (5) mit 3,3-Dimethylacrolein oder Zimtaldehyd werden 3-Methyl-1-tris(trimethylsilyl)silyl-2-butenol(1) (6) und (E)-3-Phenyl-1-tris(trimethylsilyl)silyl-2-propenol(1) (7) hergestellt, die sich als geeignete Precursoren zur Gewinnung der instabilen 1-Silabutadiene (Me3Si)2Si = CHCH = CR1R2 8 und 9 (8: R1 = R2 = Me; 9: R1 = H, R2 = Ph) nach dem Prinzip der modifizierten Peterson-Reaktion erwiesen. So eliminieren 6 und 7 nach Deprotonierung mit überschüssigem MeLi in Ether bei tiefer Temperatur Trimethylsilanolat und bilden 8 und 9, die durch das überschüssige Organolithium-Reagens durch nucleophile 1,2- und 1,4-Additionsreaktionen abgefangen werden. In Abwesenheit von Abfangreagenzien, z. B. dann, wenn 8 und 9 aus 6 und 7 durch stöchiometrische Mengen MeLi in Ether erzeugt werden, dimerisieren die freigesetzten 1-Silabutadiene im Sinne einer formalen [2 + 2]-Kopf-Kopf-Cycloaddition und man erhält die 1,2-Disilacyclobutane 17 und 18 neben Polymermaterial. Die Einwirkung von MeLi auf 6 in Tetrahydrofuran bewirkt eine 1,3-Si,O-Trimethylsilylwanderung unter Bildung des Alkoxysilans (Me3Si)2SiH—CH(OSiMe3)CH = CMe2 19.
    Notes: 3-Methyl-1-tris(trimethylsilyl)silyl-2-butenol(1) (6) and (E)-3-Phenyl-1-tris(trimethylsilyl)silyl-2-propenol(1) (7) were prepared by the reaction of tris(trimethylsilyl)silyllithium (5) with 3,3-dimethylacrolein and (E)-cinnamaldehyde, resp. The alcohols 6 and 7 proved to be suitable precursors for the generation of the transient 1-silabutadienes (Me3Si)2Si = CHCH = CR1R2 8 and 9 (8: R1 = R2 = Me; 9: R1 = H, R2 = Ph) following the principle of the modified Peterson reaction. Thus, 6 and 7 after deprotonation with excess MeLi in ether at low temperatures eliminated trimethylsilanolate and gave 8 and 9, which were trapped by the excess organolithium reagent undergoing nucleophilic 1,2- or 1,4-addition reactions. In the absence of scavengers, e.g. when 8 and 9 were generated by treatment of 6 and 7 with stoichiometric quantities of MeLi in ether, the 1-silabutadienes dimerize in a [2 + 2] head-to-head fashion to give the 1,2-disilacyclobutanes 17 and 18, resp., besides polymeric material. Treatment of the alcohol 6 with MeLi in tetrahydrofuran caused a 1,3-Si,O-trimethylsilyl shift affording the alkoxysilane (Me3Si)2SiH—CH(OSiMe3)CH = CMe2 19.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/zaac.19966220509
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  • 10
    Electronic Resource
    Electronic Resource
    Controlled Conversion of the Transient 2-Mesityl-1,1-bis(trimethylsilyl)silene into a Tetrahydro-2,3-disilanaphthalene, a 1,2-Disilacyclobutane, or a 1,3-Disilacyclobutane (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 1083-1088 
    Details
    ISSN: 0009-2940
    Keywords: Silenes ; Silene dimerization ; 1,2-Disilacyclobutanes ; 1,3-Disilacyclobutanes ; 2,3-Disilanaphthalene, tetrahydro- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mesityl[tris(trimethylsilyl)silyl]methanol (1) reacts with strong bases with elimination of trimethylsilanolate according to a Peterson-type mechanism, the outcome of the reaction being dependent on solvent, temperature, and nature of the organometallic base applied. Thus, 1 was converted by treatment with MeLi in ether at -78°C to (E)-1,2,3,8a-tetra -hydro-1-mesityl-5,7,8a-trimethyl-2,2,3,3-tetrakis (trimethylsi-lyl)-2,3-disilanaphthalene (3), formally a [2 + 4] cyclodimer of the transient silene (Me3Si)2Si=CHMes (2). The reaction of 1 with PhMgBr in THF after some days resulted in the formation of (Z)-3,4-dimesityl-1,1,2,2-tetrakis(trimethylsilyl) -1,2-disilacyclobutane (6) as the main product besides small quantities of 3, the polysilane (Me3SiSi(SiMe3)2CH2Mes (10), and the alkoxysilane (Me3Si)3SiCH(Mes)OSi(Si-Me3)2CH2Mes (7). Compound 6, the formal [2 + 2] cycloadduct of 2, can also be obtained by thermal treatment of 3 and is considered to be the thermodynamically more stable silene dimer whereas 3 is the kinetically preferred product. At high LiBr concentrations in the reaction mixture 1 was converted by PhMgBr in THF to (E)-2,4-dimesityl-1,1,3,3-tetrakis(tri- methylsilyl)-1,3-disilacyclobutane (13) besides 6 and [bis(tri-methylsilyl)silyl]mesityl(trimethylsiloxy)methane (11). The unforeseen formation of 13 is discussed as proceeding via the silene-lithium bromide adduct (Me3Si)2Si(Br)CH(Li)Mes (12). In the absence of LiBr 1 was converted by MeLi in THF at -78°C to 11 and the trisilane (Me3Si)2Si(Me)CH2Mes (4b). Probable pathways of the formation of all new compounds are discussed. For 6 and 13 the results of the X-ray structural analyses are given.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951281105
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