原子贡献法估算硅烷及硅氧烷的摩尔折射度
|
摘要
根据硅烷和硅氧烷的分子结构,利用原子贡献法考察了中心Si原子及与其相连接的不同原子(C、H、Cl、O)和官能团(苯基和碳碳双键)的摩尔折射度,以110种硅烷和硅氧烷折射率和密度实验数据对建立的摩尔折射度估算方程进行了关联,利用SPSS 19.0软件对摩尔折射度方程组进行了拟合,得到上述原子和官能团的摩尔折射度数值,110种化合物摩尔折射度计算值与文献值之间的总体平均绝对误差、平均相对误差及均方根误差分别为0.227cm3.mol-1、0.433%及0.369cm3·mol-1,为已知结构有机硅新化合物折射率的预测或特定折射率有机硅化合物的设计合成提供了依据.
The molar refraction of the central Si atom and different atoms(C,H,O,Cl)as well as or functional groups(phenyl group and C=C double bond)that directly connected with the central Si atom in silane or siloxane molecules was investigated by atom contribution method.The molar refraction values and density experimental data of 110 kinds of silanes and siloxanes were used to correlate with the established estimation formula of molar refraction.The equation set of molar refraction was fitted by SPSS 19.0software and the values of molar refraction of each studied atoms and groups were estimated.The overall mean absolute error,the mean relative error and the root-mean-square deviation between the estimated and calculated values of the molar refraction of 110 kinds of chemicals were 0.227cm3.mol-1,0.433%and 0.369 cm3·mol-1,respectively.The results are beneficial to the prediction of the refractive index of the novel silicone compounds with known structure or the design and synthesis of the novel silicone compounds with specific refractive index.
The molar refraction of the central Si atom and different atoms(C,H,O,Cl)as well as or functional groups(phenyl group and C=C double bond)that directly connected with the central Si atom in silane or siloxane molecules was investigated by atom contribution method.The molar refraction values and density experimental data of 110 kinds of silanes and siloxanes were used to correlate with the established estimation formula of molar refraction.The equation set of molar refraction was fitted by SPSS 19.0software and the values of molar refraction of each studied atoms and groups were estimated.The overall mean absolute error,the mean relative error and the root-mean-square deviation between the estimated and calculated values of the molar refraction of 110 kinds of chemicals were 0.227cm3.mol-1,0.433%and 0.369 cm3·mol-1,respectively.The results are beneficial to the prediction of the refractive index of the novel silicone compounds with known structure or the design and synthesis of the novel silicone compounds with specific refractive index.
引文
[1]王克强.硅烷摩尔折射度与其分子结构之间关系的探讨[J].有机化学,1994,14(3):269-274.
[2]王克强.应用基团键贡献法预测烷烃、脂肪醇和硫醇的摩尔折射度[J].韩山师范学院学报,2000,21(2):66-70.
[3]王从岗,陈泽辉,富嘉文,等.基团贡献法预测石油馏分热力学性质的探索[J].石油炼制与化工,1993,24(5):57-64.
[4]Speight J G.Langes Handbook of Chemistry[M].16th ed.New York:McGraw-Hill Companies,Inc.,2004.
[5]Kupchik E J.Structure-Molar Refraction Relationships of Alkylsilanes Using Molecular Connectivity[J].Quantitative structure-activity relationships in pharmacology,chemistry,and biology,1985,4(3):123-127.
[6]Hall L H,Aaserud D.Structure-activity models for molar refraction of alkylsilanes based on molecular connectivity[J].Quantitative Structure-Activity Relationships,1989,8(4):296-304.
[7]Krolevets A A.New syntheses of alkoxysilanes and their properties[J].Zhurnal Obshchei Khimii,1988,58(10):2274-2281.
[8]Metal-Organics Catalog[M].Gelest,Inc.:Morrisville,PA,2007.
[9]Dolgov B N,Voronkov M G,Borisov S N.Catalytic transformations of alkyldichlorosilanes and dialkylchlorosilanes in the presence of a-luminum chloride[J].Zhurnal Obshchei Khimii,1957,27:709-716.
[10]Kanazashi M.Unsaturated organosilicon compounds.II.Reactions and properties of vinyltrimethylsilane[J].Bulletin of the Chemical Society of Japan,1955,28(1):44-50.
[11]Borisov S N,Sviridova N G.Cleavage of siloxanes by halosilanes.A new method of synthesis of organosiloxanes[J].Zhurnal Obshchei Khimii,1959,29:1534-1541.
[12]Freidlina R K,Chukovskaya E T,Tsao I.Addition of silanes to unsaturated compounds in the presence of iron pentacarbonyl[J].Doklady Akademii Nauk SSSR,1959,127:352-355.
[13]Dolgov B N,Borisov S N,Voronkov M G.Reaction of dialkylchlorosilanes with aluminum chloride[J].Zhurnal Obshchei Khimii,1957,27:2062-2066.
[14]Valade J,Calas R,Mileo J C.Organosilicon chemistry.Preparation of trialkylchlorosilanes[J].Compt Rend.1959,249:1769-1770.
[15]Nametkin N C,Sorokin G V,Pozdnyakova M V,et al.Polymerization of ethylene with the titanium tetrachloride-trialkyl aluminum-trialkylsilane systems[J].Vysokomolekulyarnye Soedineniya,Seriya B:Kratkie Soobshcheniya,1968,10(1):53-55.
[16]Petrov A D.Synthesis ofα-trimethylsilylstyrene,1-trimethylsilylcyclohexene,and other unsaturated organosilicon compounds[J].Zhurnal Obshchei Khimii,1957,27:1535-1539.
[17]Dolgov B N,Vinter G,Komarov V A,et al.Reaction of pentaerythritol with trialkylsilanes in presence of certain metal halides[J].Bulletin of the Academy of Sciences of the USSR,Division of chemical science,1963,12(12):1978-1983.
[18]Sheludyakov V D.Characteristics of hydrochlorination of vinylsilanes with several vinyl groups at the silicon atom[J].Zhurnal Obsh-chei Khimii,1985,55:1345-1350.
[19]Vaisarova V,Chvalovsky V.Organosilicon compounds.LVI.Dipole moments of substituted vinylsilanes and phenylsilanes[J].Col-lection of Czechoslovak Chemical Communications,1968,33(3):859-865.
[20]Voronkov M G.Acetylene hydrosilylation reaction[J].Doklady Akademii Nauk SSSR,1980,254:887-890.
[21]Mironov V F.Relative reactivity of some alkenylsilanes with trichlorosilane[J].Izvestiya Akademii Nauk SSSR,Seriya Khimi-cheskaya,1960,4:760-762.
[22]Sommer L H,Bailey D L,Goldberg G M.Vinylsilanes,chlorovinylsilanes,andβ-styryltrimethylsilane.Further studies on theα-sili-con effect and β-eliminations involving silicon[J].Journal of the American Chemical Society,1954,76(6):1613-1618.
[23]Kanazashi M.Unsaturated organosilicon compounds.I.Synthesis of organovinylsilanes by Wurtz-Fittig reaction[J].Bulletin of theChemical Society of Japan,1953,26(9):493-496.
[24]Steiling L,Wannagat U.Sila drugs,15.Synthesis and properties of silapridinol[J].Zeitschrift fuer Naturforschung,Teil B:Anorga-nische Chemie,Organische Chemie,1979,34B:1413-1417.
[25]Mironov V F,Petrov A D,Maksimova N G.Organomagnesium synthesis of 2-and 3-(Trimethylsilyl)acrylic acids and vinyl derivatives of silicon,germanium,and tin[J].Russian Chemical Bulletin,1959,8(11):1864-1870.
[26]Sheludyakov V D,Zhun V I,Polyakova M V,et al.Some data on the synthesis of vinylsilanes[J].Zhurnal Obshchei Khimii Some data on the synthesis of vinylsilanes,1980,50(4):868-871.
[27]Zakharkin L I.Reduction of alkylc hlorosilanes with sodium hydride in the presence of triethylaluminum[J].Russian Chemical Bulletin,1960,9(12):2079-2080.
[28]Molchanova T V,Kopylov A I,Burde N L,et al.Synthesis of some aromatic silanes[J].Trudy Khimiko-Metallurgicheskogo Institu-ta,Akademiya Nauk Kazakhskoi SSR,1966,13:17-24.
[29]Lehnert R,Porzel A,Ruehlmann K.Preparation of siloxanes.9.Position of the equilibrium chlorodimethylphenylsilane+water.dblharw.hydroxydimethylphenylsilane+hydrochloric acid in dioxane-benzene-d6[J].Zeitschrift fuer Chemie,1988,28(5):190-192.
[30]Ruehlmann K,Grosse-Ruyken H,Scheller D,et al.Synthesis of siloxanes.XIV.Reaction of chlorosilanes with silanols in acid medi-um[J].Journal of Organometallic Chemistry,1988,356(1):39-47.
[31]Malnova G N,Mikheev E P,Klebansky A L,et al.Catalytic phenylation of hydrogen-containing alkylchlorosilanes with benzene[J].Doklady Akademii Nauk SSSR,1957,117:623-625.
[32]Westermark H.Preparation of some organic silicon hydrides[J].Acta Chemica Scandinavica,1954,8(10):1830-1834.
[33]Smith B.Silico ovrddot organic compounds[J].Doktorsavhandl.Chalmers Tek Hogskola,1951,6:154.
[34]Lukevics E,Pudova O A,Dzintara M.Organometallic derivatives of sulfur-containing heterocycles.XIII.Dehydrocondensation of thienylsilanes with hydroxyl-containing compounds in the presence of organic bases[J].Zhurnal Obshchei Khimii,1984,54(2):339-342.
[35]Koristek S,Langner J,Cermak J.Preparing organoalkoxysilanes and organoaryloxysilanes:Czech,CS 122624[P].1967-04-15.
[36]Voronkov M G.Alkoxysilanes.XIII.Reaction of siloxanes with alkoxysilanes.New method of synthesis of alkoxysilanes and silox-anes[J].Zhurnal Obshchei Khimii,1959,29:907-915.
[37]Andrianov K A,Delazari N V.Reactions of chloro(trimethylsiloxy)silanes[J].Russian Chemical Bulletin,1961,10(12):2028-2031.
[38]Müller R,Khne R,Sliwinski S.et al.Methylsiloxanes with Si-H bonds[J].Journal fuer Praktische Chemie(Leipzig),1960,11:336-340.
[39]Tanaka T,Tasaka A,Okawara R,et al.Lower members of methylmethoxypolysiloxanes with one to five silicon atoms[J].Technolo-gy Reports of the Osaka University,1957,7:193-197.
[40]Krolevets A A,Antipova V V,Popov A G,et al.New syntheses of alkoxysilanes and their properties[J].Zhurnal Obshchei Khimii,1988,58(10):2274-2281.
[41]Greber G,Metzinger L.Polysiloxane hydrides:DE,1085875[P].1960-07-28.
[42]Lebedev E P,Fedorov A D.Cocondensation of organodisilazanes and organochlorosilanes with organosilanols and siloxanols[J].Zhur-nal Obshchei Khimii,1979,49(1):147-150.
[43]Kovalev I F,Ozolins L,Voronkov M G,et al.Integral intensities and depolarization ratios of Raman lines of(CH3)3SiOSi(CH3)3,(CH3)3SiOC(CH3)3,and(CH3)3COC(CH3)3[J].Akademiya Nauk SSSR,Otdelenie Fiziko-Matematicheskikh Nauk,1967,3:301-307.
[44]Andreev D N,Kukharskaya E V.Condensation of hexamethyldisiloxane in a high-voltage silent discharge of sonic frequency[J].Doklady Akademii Nauk SSSR,1960,134:817-820.
[45]Mironov I V,Siraeva I N,Kiladze T K,et al.Hydrosilylation of 4,4-dimethyl-1,3-dioxane[J].Zhurnal Obshchei Khimii,1981,51(12):2700-2704.
[46]Andrianov K A,Kochetkova A S,Khananashvili L M.Copolymerization of methylvinylsiloxane oligomers with methylhydridosilox-anes[J].Zhurnal Obshchei Khimii,1968,38(1):175-178.
[47]Petrov A D,Vdovin V M.Reaction of symmetric tetraalkyldisiloxanes with dialkyldialkenylsilanes and symmetric tetraalkyldialkenyld-isiloxanes[J].Izvestiya Akademii Nauk SSSR,Seriya Khimicheskaya,1959,4:939-941.
[48]McCusker P A,Ostdick T.Reactions of haloboranes with organocyclosiloxanes.I.Boron chloride with methyl and ethyl trimer andtetramer[J].Journal of the American Chemical Society,1958,80(5):1103-1106.
[49]Borisov S N,Sviridova N G,Orlova V S.Reaction of silanols with hydrosilanes[J].Zhurnal Obshchei Khimii,1966,36(4):687-692.
[50]Sliwinski S.Silicones.XCVI.Preparation of 1,3,3,5-tetramethyl-1,1,5,5-tetraphenyl-and 1,3,5-trimethyl-1,1,3,5,5-pentaphenyl-trisiloxane[J].Journal fuer Praktische Chemie(Leipzig),1966,32(1-2):31-36.
[51]Andreev D N,Lavrinovich L I.Resistance of Si-C bonds in dimethyldialkylsilanes to the action of sulfuric acid[J].Zhurnal ObshcheiKhimii,1968,38(12):2743-2751.
[52]Topchiev A V,Nametkin N S,Kartasheva L I.Reaction of ethyl bromide with silicon[J].Russian Chemical Bulletin,1958,7(8):922-925.
[53]Sadykh-Zade S I,Petrov A D.Synthesis and reactions of butadienylsilanes[J].Zhurnal Obshchei Khimii,1958,28:1542-1547.
[54]Patnode W I,Wilcock D F.Methylpolysiloxanes[J].Journal of the American Chemical Society,1946,68:358-363.
[55]Borisov S N,Voronkov M G,Dolgov B N.The disproportionation of trialkylsilanes[J].Bulletin of the Academy of Sciences of theUSSR,Division of chemical science,1957,6(11):1416-1418.
[56]Westermark H.The exchange of ethoxy groups in methylethoxysilanes for alkyl groups[J].Svensk Kemisk Tidskrift,1952,64:283-284.
[57]Ponomarenko V A,Sokolov B A,Petrov A D.Addition of methyldichlorosilane and ethyldichlorosilane to allyl halides[J].DokladyAkademii Nauk SSSR,1956,106:76-79.
[58]Andrianov K A,Gavrikova L A,Rodionova E F.Synthesis and investigation of polymerization reactions of divinylsiloxane oligomersand their copolymerization with isoprene[J].Izvestiya Akademii Nauk SSSR,Seriya Khimicheskaya,1968,8:1786-1791.
[59]Brevnova T N,Semenov V V.Oxidation of 1-phenyl-2-chlorotetramethyldisilane by peroxide compounds[J].Zhurnal ObshcheiKhimii,1979,49(1):142-147.
[60]Andrianov K A,Nogaideli A I,Nakaidze L I.Reaction of 1,5-dihydroorganotrisiloxanes with organohydroxysilanes[J].Izvestiya Aka-demii Nauk SSSR,Seriya Khimicheskaya,1968,9:2146-2147.
[61]Kumada M.Preparation of ethoxychlorosilanes and their alkyl derivatives by ethoxy-chlorine interconversions[J].Journal of the Insti-tute of Polytechnics,Osaka City University,1952,2(Ser.C):139-146.
[62]Alksne V,Grinevich K P.Alkenylalkoxychlorosilanes[J].Latvijas PSR Zinatnu Akademijas Vestis,Kimijas Serija,1964,(2):249-252.
[63]McCusker P A,Ostdick T.Reactions of haloboranes with organocyclosiloxanes.I.Boron chloride with methyl and ethyl trimer andtetramer[J].Journal of the American Chemical Society,1958,80:1103-1106.
[64]Andrianov K A,Zhdanov A A,Kashutina E A.Reaction of diethylmethoxychlorosilane with sodium derivatives of acetylacetone and acetoacetic ester[J].Zhurnal Obshchei Khimii,1962,32:297-301.
[65]Dow Corning LTD.Improvements in or relating to the manufacture of co-polymeric siloxanes:GB,659012[P].1951-10-17.
[2]王克强.应用基团键贡献法预测烷烃、脂肪醇和硫醇的摩尔折射度[J].韩山师范学院学报,2000,21(2):66-70.
[3]王从岗,陈泽辉,富嘉文,等.基团贡献法预测石油馏分热力学性质的探索[J].石油炼制与化工,1993,24(5):57-64.
[4]Speight J G.Langes Handbook of Chemistry[M].16th ed.New York:McGraw-Hill Companies,Inc.,2004.
[5]Kupchik E J.Structure-Molar Refraction Relationships of Alkylsilanes Using Molecular Connectivity[J].Quantitative structure-activity relationships in pharmacology,chemistry,and biology,1985,4(3):123-127.
[6]Hall L H,Aaserud D.Structure-activity models for molar refraction of alkylsilanes based on molecular connectivity[J].Quantitative Structure-Activity Relationships,1989,8(4):296-304.
[7]Krolevets A A.New syntheses of alkoxysilanes and their properties[J].Zhurnal Obshchei Khimii,1988,58(10):2274-2281.
[8]Metal-Organics Catalog[M].Gelest,Inc.:Morrisville,PA,2007.
[9]Dolgov B N,Voronkov M G,Borisov S N.Catalytic transformations of alkyldichlorosilanes and dialkylchlorosilanes in the presence of a-luminum chloride[J].Zhurnal Obshchei Khimii,1957,27:709-716.
[10]Kanazashi M.Unsaturated organosilicon compounds.II.Reactions and properties of vinyltrimethylsilane[J].Bulletin of the Chemical Society of Japan,1955,28(1):44-50.
[11]Borisov S N,Sviridova N G.Cleavage of siloxanes by halosilanes.A new method of synthesis of organosiloxanes[J].Zhurnal Obshchei Khimii,1959,29:1534-1541.
[12]Freidlina R K,Chukovskaya E T,Tsao I.Addition of silanes to unsaturated compounds in the presence of iron pentacarbonyl[J].Doklady Akademii Nauk SSSR,1959,127:352-355.
[13]Dolgov B N,Borisov S N,Voronkov M G.Reaction of dialkylchlorosilanes with aluminum chloride[J].Zhurnal Obshchei Khimii,1957,27:2062-2066.
[14]Valade J,Calas R,Mileo J C.Organosilicon chemistry.Preparation of trialkylchlorosilanes[J].Compt Rend.1959,249:1769-1770.
[15]Nametkin N C,Sorokin G V,Pozdnyakova M V,et al.Polymerization of ethylene with the titanium tetrachloride-trialkyl aluminum-trialkylsilane systems[J].Vysokomolekulyarnye Soedineniya,Seriya B:Kratkie Soobshcheniya,1968,10(1):53-55.
[16]Petrov A D.Synthesis ofα-trimethylsilylstyrene,1-trimethylsilylcyclohexene,and other unsaturated organosilicon compounds[J].Zhurnal Obshchei Khimii,1957,27:1535-1539.
[17]Dolgov B N,Vinter G,Komarov V A,et al.Reaction of pentaerythritol with trialkylsilanes in presence of certain metal halides[J].Bulletin of the Academy of Sciences of the USSR,Division of chemical science,1963,12(12):1978-1983.
[18]Sheludyakov V D.Characteristics of hydrochlorination of vinylsilanes with several vinyl groups at the silicon atom[J].Zhurnal Obsh-chei Khimii,1985,55:1345-1350.
[19]Vaisarova V,Chvalovsky V.Organosilicon compounds.LVI.Dipole moments of substituted vinylsilanes and phenylsilanes[J].Col-lection of Czechoslovak Chemical Communications,1968,33(3):859-865.
[20]Voronkov M G.Acetylene hydrosilylation reaction[J].Doklady Akademii Nauk SSSR,1980,254:887-890.
[21]Mironov V F.Relative reactivity of some alkenylsilanes with trichlorosilane[J].Izvestiya Akademii Nauk SSSR,Seriya Khimi-cheskaya,1960,4:760-762.
[22]Sommer L H,Bailey D L,Goldberg G M.Vinylsilanes,chlorovinylsilanes,andβ-styryltrimethylsilane.Further studies on theα-sili-con effect and β-eliminations involving silicon[J].Journal of the American Chemical Society,1954,76(6):1613-1618.
[23]Kanazashi M.Unsaturated organosilicon compounds.I.Synthesis of organovinylsilanes by Wurtz-Fittig reaction[J].Bulletin of theChemical Society of Japan,1953,26(9):493-496.
[24]Steiling L,Wannagat U.Sila drugs,15.Synthesis and properties of silapridinol[J].Zeitschrift fuer Naturforschung,Teil B:Anorga-nische Chemie,Organische Chemie,1979,34B:1413-1417.
[25]Mironov V F,Petrov A D,Maksimova N G.Organomagnesium synthesis of 2-and 3-(Trimethylsilyl)acrylic acids and vinyl derivatives of silicon,germanium,and tin[J].Russian Chemical Bulletin,1959,8(11):1864-1870.
[26]Sheludyakov V D,Zhun V I,Polyakova M V,et al.Some data on the synthesis of vinylsilanes[J].Zhurnal Obshchei Khimii Some data on the synthesis of vinylsilanes,1980,50(4):868-871.
[27]Zakharkin L I.Reduction of alkylc hlorosilanes with sodium hydride in the presence of triethylaluminum[J].Russian Chemical Bulletin,1960,9(12):2079-2080.
[28]Molchanova T V,Kopylov A I,Burde N L,et al.Synthesis of some aromatic silanes[J].Trudy Khimiko-Metallurgicheskogo Institu-ta,Akademiya Nauk Kazakhskoi SSR,1966,13:17-24.
[29]Lehnert R,Porzel A,Ruehlmann K.Preparation of siloxanes.9.Position of the equilibrium chlorodimethylphenylsilane+water.dblharw.hydroxydimethylphenylsilane+hydrochloric acid in dioxane-benzene-d6[J].Zeitschrift fuer Chemie,1988,28(5):190-192.
[30]Ruehlmann K,Grosse-Ruyken H,Scheller D,et al.Synthesis of siloxanes.XIV.Reaction of chlorosilanes with silanols in acid medi-um[J].Journal of Organometallic Chemistry,1988,356(1):39-47.
[31]Malnova G N,Mikheev E P,Klebansky A L,et al.Catalytic phenylation of hydrogen-containing alkylchlorosilanes with benzene[J].Doklady Akademii Nauk SSSR,1957,117:623-625.
[32]Westermark H.Preparation of some organic silicon hydrides[J].Acta Chemica Scandinavica,1954,8(10):1830-1834.
[33]Smith B.Silico ovrddot organic compounds[J].Doktorsavhandl.Chalmers Tek Hogskola,1951,6:154.
[34]Lukevics E,Pudova O A,Dzintara M.Organometallic derivatives of sulfur-containing heterocycles.XIII.Dehydrocondensation of thienylsilanes with hydroxyl-containing compounds in the presence of organic bases[J].Zhurnal Obshchei Khimii,1984,54(2):339-342.
[35]Koristek S,Langner J,Cermak J.Preparing organoalkoxysilanes and organoaryloxysilanes:Czech,CS 122624[P].1967-04-15.
[36]Voronkov M G.Alkoxysilanes.XIII.Reaction of siloxanes with alkoxysilanes.New method of synthesis of alkoxysilanes and silox-anes[J].Zhurnal Obshchei Khimii,1959,29:907-915.
[37]Andrianov K A,Delazari N V.Reactions of chloro(trimethylsiloxy)silanes[J].Russian Chemical Bulletin,1961,10(12):2028-2031.
[38]Müller R,Khne R,Sliwinski S.et al.Methylsiloxanes with Si-H bonds[J].Journal fuer Praktische Chemie(Leipzig),1960,11:336-340.
[39]Tanaka T,Tasaka A,Okawara R,et al.Lower members of methylmethoxypolysiloxanes with one to five silicon atoms[J].Technolo-gy Reports of the Osaka University,1957,7:193-197.
[40]Krolevets A A,Antipova V V,Popov A G,et al.New syntheses of alkoxysilanes and their properties[J].Zhurnal Obshchei Khimii,1988,58(10):2274-2281.
[41]Greber G,Metzinger L.Polysiloxane hydrides:DE,1085875[P].1960-07-28.
[42]Lebedev E P,Fedorov A D.Cocondensation of organodisilazanes and organochlorosilanes with organosilanols and siloxanols[J].Zhur-nal Obshchei Khimii,1979,49(1):147-150.
[43]Kovalev I F,Ozolins L,Voronkov M G,et al.Integral intensities and depolarization ratios of Raman lines of(CH3)3SiOSi(CH3)3,(CH3)3SiOC(CH3)3,and(CH3)3COC(CH3)3[J].Akademiya Nauk SSSR,Otdelenie Fiziko-Matematicheskikh Nauk,1967,3:301-307.
[44]Andreev D N,Kukharskaya E V.Condensation of hexamethyldisiloxane in a high-voltage silent discharge of sonic frequency[J].Doklady Akademii Nauk SSSR,1960,134:817-820.
[45]Mironov I V,Siraeva I N,Kiladze T K,et al.Hydrosilylation of 4,4-dimethyl-1,3-dioxane[J].Zhurnal Obshchei Khimii,1981,51(12):2700-2704.
[46]Andrianov K A,Kochetkova A S,Khananashvili L M.Copolymerization of methylvinylsiloxane oligomers with methylhydridosilox-anes[J].Zhurnal Obshchei Khimii,1968,38(1):175-178.
[47]Petrov A D,Vdovin V M.Reaction of symmetric tetraalkyldisiloxanes with dialkyldialkenylsilanes and symmetric tetraalkyldialkenyld-isiloxanes[J].Izvestiya Akademii Nauk SSSR,Seriya Khimicheskaya,1959,4:939-941.
[48]McCusker P A,Ostdick T.Reactions of haloboranes with organocyclosiloxanes.I.Boron chloride with methyl and ethyl trimer andtetramer[J].Journal of the American Chemical Society,1958,80(5):1103-1106.
[49]Borisov S N,Sviridova N G,Orlova V S.Reaction of silanols with hydrosilanes[J].Zhurnal Obshchei Khimii,1966,36(4):687-692.
[50]Sliwinski S.Silicones.XCVI.Preparation of 1,3,3,5-tetramethyl-1,1,5,5-tetraphenyl-and 1,3,5-trimethyl-1,1,3,5,5-pentaphenyl-trisiloxane[J].Journal fuer Praktische Chemie(Leipzig),1966,32(1-2):31-36.
[51]Andreev D N,Lavrinovich L I.Resistance of Si-C bonds in dimethyldialkylsilanes to the action of sulfuric acid[J].Zhurnal ObshcheiKhimii,1968,38(12):2743-2751.
[52]Topchiev A V,Nametkin N S,Kartasheva L I.Reaction of ethyl bromide with silicon[J].Russian Chemical Bulletin,1958,7(8):922-925.
[53]Sadykh-Zade S I,Petrov A D.Synthesis and reactions of butadienylsilanes[J].Zhurnal Obshchei Khimii,1958,28:1542-1547.
[54]Patnode W I,Wilcock D F.Methylpolysiloxanes[J].Journal of the American Chemical Society,1946,68:358-363.
[55]Borisov S N,Voronkov M G,Dolgov B N.The disproportionation of trialkylsilanes[J].Bulletin of the Academy of Sciences of theUSSR,Division of chemical science,1957,6(11):1416-1418.
[56]Westermark H.The exchange of ethoxy groups in methylethoxysilanes for alkyl groups[J].Svensk Kemisk Tidskrift,1952,64:283-284.
[57]Ponomarenko V A,Sokolov B A,Petrov A D.Addition of methyldichlorosilane and ethyldichlorosilane to allyl halides[J].DokladyAkademii Nauk SSSR,1956,106:76-79.
[58]Andrianov K A,Gavrikova L A,Rodionova E F.Synthesis and investigation of polymerization reactions of divinylsiloxane oligomersand their copolymerization with isoprene[J].Izvestiya Akademii Nauk SSSR,Seriya Khimicheskaya,1968,8:1786-1791.
[59]Brevnova T N,Semenov V V.Oxidation of 1-phenyl-2-chlorotetramethyldisilane by peroxide compounds[J].Zhurnal ObshcheiKhimii,1979,49(1):142-147.
[60]Andrianov K A,Nogaideli A I,Nakaidze L I.Reaction of 1,5-dihydroorganotrisiloxanes with organohydroxysilanes[J].Izvestiya Aka-demii Nauk SSSR,Seriya Khimicheskaya,1968,9:2146-2147.
[61]Kumada M.Preparation of ethoxychlorosilanes and their alkyl derivatives by ethoxy-chlorine interconversions[J].Journal of the Insti-tute of Polytechnics,Osaka City University,1952,2(Ser.C):139-146.
[62]Alksne V,Grinevich K P.Alkenylalkoxychlorosilanes[J].Latvijas PSR Zinatnu Akademijas Vestis,Kimijas Serija,1964,(2):249-252.
[63]McCusker P A,Ostdick T.Reactions of haloboranes with organocyclosiloxanes.I.Boron chloride with methyl and ethyl trimer andtetramer[J].Journal of the American Chemical Society,1958,80:1103-1106.
[64]Andrianov K A,Zhdanov A A,Kashutina E A.Reaction of diethylmethoxychlorosilane with sodium derivatives of acetylacetone and acetoacetic ester[J].Zhurnal Obshchei Khimii,1962,32:297-301.
[65]Dow Corning LTD.Improvements in or relating to the manufacture of co-polymeric siloxanes:GB,659012[P].1951-10-17.