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Volumn 351, Issue 9, 2009, Pages 1405-1411

An efficient solvent-free route to silyl esters and silyl ethers

Author keywords

Alcohols; Carboxylic acids; Dehydrosilylation; Ruthenium; Silyl esters; Silyl ethers

Indexed keywords


EID: 67549099238     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900230     Document Type: Article
Times cited : (61)

References (53)
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    • g) G.-B. Liu, Synlett 2006, 9, 1431;
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    • Liu, G.-B.1
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    • It was confirmed by the DLS measurements of the reaction solutions that no ruthenium clusters (detection limit: 0.6 nm) were detected during the dehydrosilylation.
    • It was confirmed by the DLS measurements of the reaction solutions that no ruthenium clusters (detection limit: 0.6 nm) were detected during the dehydrosilylation.
  • 41
    • 67549109928 scopus 로고    scopus 로고
    • For solid carboxylic acids, toluene or 1,4-dioxane was used as a solvent
    • For solid carboxylic acids, toluene or 1,4-dioxane was used as a solvent.
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    • Lee and co-workers have reported the efficient synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes.[4k] The synthesis consists of two consecutive reactions of silylation of the terminal alkenyl alcohols with alkynylsilanes followed by the intramolecular methathesis, and [RuCl2(p-cymene)]2 is used for the former silylation.[4k] Although the silylation of alkenyl and alkynyl alcohols is reported in the literature, the applicability to aliphatic and benzylic alcohols as well as carboxylic acids is not mentioned.[4k
    • [4k]
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    • 2 with respect to the corresponding silyl ethers were also formed.
    • 2 with respect to the corresponding silyl ethers were also formed.
  • 45
    • 0034614043 scopus 로고    scopus 로고
    • A similar mechanism has been reported for the hydrolytic oxidation of silanes with water: a M. Lee, S. Ko, S. Chang, J. Am. Chem. Soc. 2000, 122, 12011;
    • A similar mechanism has been reported for the hydrolytic oxidation of silanes with water: a) M. Lee, S. Ko, S. Chang, J. Am. Chem. Soc. 2000, 122, 12011;
  • 47
    • 67549119934 scopus 로고    scopus 로고
    • S= 19.9 min, DAICEL CHIRALCEL ODH, 0.46 cm φ×0.25 cm, eluent: n-hexane) with a CD-detector: S. Shinke, T. Tsuchimoto, Y. Kawakami, Silicon Chem. 2005, 3, 243.
    • S= 19.9 min, DAICEL CHIRALCEL ODH, 0.46 cm φ×0.25 cm, eluent: n-hexane) with a CD-detector: S. Shinke, T. Tsuchimoto, Y. Kawakami, Silicon Chem. 2005, 3, 243.
  • 48
    • 67549138143 scopus 로고    scopus 로고
    • Under the conditions described in Eq. (6) (1.5 equivalents of 4b with respect to 2f), the reaction rate was very slow and the corresponding silyl ether was obtained in 30% yield after 48 h. In this case, the ee values of the product were almost unchanged during the reaction (84-88%ee).
    • Under the conditions described in Eq. (6) (1.5 equivalents of 4b with respect to 2f), the reaction rate was very slow and the corresponding silyl ether was obtained in 30% yield after 48 h. In this case, the ee values of the product were almost unchanged during the reaction (84-88%ee).
  • 49
    • 67549102766 scopus 로고    scopus 로고
    • 2 and excess amounts of alcohols. Therefore, the optical purity of the R-isomer 5s was decreased by the transetherification (racemization)in the presence of large excess amounts of 4b [Eq. (7)].
    • 2 and excess amounts of alcohols. Therefore, the optical purity of the R-isomer 5s was decreased by the transetherification (racemization)in the presence of large excess amounts of 4b [Eq. (7)].
  • 50
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    • 3rd edn, Eds, D. D. Perrin, W. L. F. Armarego, Pergamon Press, Oxford, U.K
    • Purification of Laboratory Chemicals, 3rd edn., (Eds.: D. D. Perrin, W. L. F. Armarego), Pergamon Press, Oxford, U.K., 1988.
    • (1988) Purification of Laboratory Chemicals


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.