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- W2067258889 abstract "Sequential treatment of diphenylbis((phenylthio)methyl)silane with lithium naphthalenide, hexafluoroacetone, and then aqueous NH4Cl gave the (β-hydroxyalkyl)diphenyl((phenylthio)methyl)silane 8, Ph2Si(CH2SPh)CH2C(CF3)2OH, a hydroxyl group of which was protected with methoxymethyl to afford the corresponding methoxymethyl ether 9a. Similarly, the reaction of 9a with hexafluoroacetone followed by deprotection of the methoxymethyl group yielded the diphenylbis(β-hydroxyalkyl)silane 11, Ph2Si[CH2C(CF3)2OH]2. Sequential treatment of 11 with trifluorormethanesulfonic acid in CDCl3 and with 2 mol equiv of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave almost quantitatively [DBU·H]+, phenylbis[1,1,1-trifluoro-2-(trifluoromethyl)-2-propanolate(2−)-C3,O]silicate(−1) (6) along with [DBU·H]+ triflate at low temperature (−20 °C). The 29Si NMR, which showed a signal at δSi −61.75, as well as other NMR analyses indicate that 6 is a pentacoordinate silicate with two 1,2-oxasiletanide rings. Compound 6 decomposed at room temperature to give almost quantitatively MeC(CF3)2OH after treatment with water instead of a Peterson reaction product, CH2C(CF3)2. Taking into consideration the results of a control experiment, it is strongly suggested that a novel type of silicate such as 6 can be regarded as an intermediate of a homo-Brook rearrangement." @default.
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- W2067258889 date "1998-01-06" @default.
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- W2067258889 title "Generation and Decomposition of a Pentacoordinate Spirobis[1,2-oxasiletanide]" @default.
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- W2067258889 doi "https://doi.org/10.1021/om970459a" @default.
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