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• W1997043904 endingPage "3178" @default.
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• W1997043904 abstract "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 but also the dimethylsilylene-bridged product 8a. FMe2SiSiPh2F served better in preparation of the desired 3b than ClMe2SiSiPh2Cl. The sterically hindered FPh2SiSiPh2F did not give silylation products. The X-ray structural analyses of 3a and 3b provided the first geometrical parameters of the 2,2‘-disilanylene-bridged 1,1‘-binaphthyl derivatives. In comparison with the acyclic analogues and less sterically hindered disilanylene-bridged biaryls such as 2,2‘-bis(trimethylsilyl)-1,1‘-binaphthyl ((±)-1a), (R)-(−)-2,2‘-bis(dimethylphenylsilyl)-1,1‘-binaphthyl ((R)-(−)-1b), dibenzo-1,1,2,2-tetramethyl-1,2-disilacyclohexa-3,5-diene (12), and dithienodisilacyclohexadiene 13 the disilanylene-bridged binaphthyls 3 were found to be highly strained due to the steric repulsion of the binaphthyl groups fixed in a narrow angle." @default.
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• W1997043904 date "2000-07-11" @default.
• W1997043904 modified "2023-09-29" @default.
• W1997043904 title "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" @default.
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• W1997043904 doi "https://doi.org/10.1021/om0001523" @default.
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