First Isolation and Full Characterization of 2,2‘-Bishalosilyl-Substituted 1,1‘-Binaphthyls: Synthesis of 2,2‘-Bis(fluorodimethylsilyl)-1,1‘-binaphthyl and X-ray Structural Analysis of Highly Strained Disilanylene-Bridged Precursors
| العنوان: | First Isolation and Full Characterization of 2,2‘-Bishalosilyl-Substituted 1,1‘-Binaphthyls: Synthesis of 2,2‘-Bis(fluorodimethylsilyl)-1,1‘-binaphthyl and X-ray Structural Analysis of Highly Strained Disilanylene-Bridged Precursors |
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| المؤلفون: | Hisahiro Hagiwara, Tomonobu Nakamura, and Masayoshi Ando, Takashi Hoshi, Toshio Suzuki |
| المصدر: | Organometallics. 19:3170-3178 |
| بيانات النشر: | American Chemical Society (ACS), 2000. |
| سنة النشر: | 2000 |
| مصطلحات موضوعية: | Steric effects, Stereochemistry, Organic Chemistry, X-ray, Phenanthrene, Cleavage (embryo), Medicinal chemistry, Inorganic Chemistry, chemistry.chemical_compound, Hydrolysis, chemistry, Siloxane, Yield (chemistry), Physical and Theoretical Chemistry |
| الوصف: | Brominative Si−Si cleavage of 3,4-disila-3,3,4,4-tetramethyl-3,4-dihydrodibenzo[c,g]phenanthrene (3a), LiAlH4 reduction of the resulting dibromide, and fluorination of the dihydride 14a thus gave 2,2‘-bis(fluorodimethylsilyl)-1,1‘-binaphthyl (7a) in high yield as the first isolated and fully characterized 2,2‘-bis(halosilyl)-1,1‘-binaphthyl. Similar conversion of the more sterically hindered 3,4-disila-3,3-dimethyl-4,4-diphenyl-3,4-dihydrodibenzo[c,g]phenanthrene (3b) also gave the corresponding bishydrosilane 14b. However, subsequent fluorination did not give the desired bisfluorosilane 7b but rather the hydrolyzed siloxane 6b. The syntheses of the disilanylene-bridged precursors 3 were effected via bis-silylation reactions of 2,2‘-dibromo-1,1‘-binaphthyl (DBBN, 2) with dihalodisilanes ClMe2SiSiMe2Cl, ClMe2SiSiPh2Cl, FMe2SiSiPh2F, and FPh2SiSiPh2F. Although ClMe2SiSiMe2Cl predominately gave the disilanylene-bridged product 3a, XMe2SiSiPh2X (X = F, Cl) produced not only the disilanylene-bridged product 3b... |
| تدمد: | 1520-6041 0276-7333 |
| DOI: | 10.1021/om0001523 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::c0a12cae6280276700bb49bcadc874fd https://doi.org/10.1021/om0001523 |
| رقم الانضمام: | edsair.doi...........c0a12cae6280276700bb49bcadc874fd |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15206041 02767333 |
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| DOI: | 10.1021/om0001523 |