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Volumn 64, Issue 11, 2006, Pages 1148-1158

Epoxysilane rearrangement: Mechanistic studies and synthetic applications

Author keywords

[No Author keywords available]

Indexed keywords

EPOXY RESINS; NEGATIVE IONS; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

EID: 33846398509     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.64.1148     Document Type: Article
Times cited : (8)

References (91)
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    • For reviews on base-promoted isomerization of epoxides, see: a
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    • For a base-promoted ring-opening of functionalized epoxides, see: (epoxy nitriles) (a) Fleming, F. F.; Wang, Q.; Steward, O. W. J. Org. Chem. 2001, 66, 2171. (epoxy amides)
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    • Although the possibility of a silicate transition state cannot be ruled out, we believe that the species is likely to be involved on the basis of results of our previous work and calculations22 of the structure in the gas phase. Tanaka, K, Masu, H, Yamaguchi, K, Takeda, K. Tetrahedron Lett. 2005, 46, 6429
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    • Elimination reactions of α-oxidosilanes with a β-leaving group are known to proceed in an
    • Elimination reactions of α-oxidosilanes with a β-leaving group are known to proceed in an anti manner. Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. J. Am. Chem. Soc. 1985, 107, 4260-4264.
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    • For discussions on stereochemistry of Brook rearrangement of α-silyl alkoxides bearing an α, β-leaving group, see: Reich, H. J.; Holtan, R. C.; Bolm, C. J. Am. Chem. Soc. 1990, 112, 5609.
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    • Cyclopropane ring-opening by a carbanion generated by Brook rearrangement has recently been reported. Clayden, J, Watson, D. W, Chambers, M. Tetrahedron 2005, 61, 3195
    • Cyclopropane ring-opening by a carbanion generated by Brook rearrangement has recently been reported. Clayden, J.; Watson, D. W.; Chambers, M. Tetrahedron 2005, 61, 3195.
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    • Treatment of pyridin-2-sulfinyl derivative with NAHMDS in the presence of benzyl bromide afforded a complex mixture Although a similar result was obtained with both phenylsulfonyl and p-toluenesulfonyl derivatives, the latter is superior in terms of crystallizability.
    • Treatment of pyridin-2-sulfinyl derivative with NAHMDS in the presence of benzyl bromide afforded a complex mixture Although a similar result was obtained with both phenylsulfonyl and p-toluenesulfonyl derivatives, the latter is superior in terms of crystallizability.
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    • and ref. 20. For a silicate intermediate in Brook rearrangement, see
    • For a silicate intermediate in Brook rearrangement, see: Takeda, K.; Yamawaki, K.; Hatakeyama, N. J. Org. Chem. 2002, 67, 1786. and ref. 20.
    • (2002) J. Org. Chem , vol.67 , pp. 1786
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    • The use of lithium and sodium enolates resulted in recovery of the starting material and a lower yield of 14, respectively
    • The use of lithium and sodium enolates resulted in recovery of the starting material and a lower yield of 14, respectively.
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    • For reviews on [2,3]-Wittig rearrangement, see: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885.
    • For reviews on [2,3]-Wittig rearrangement, see: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885.
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    • To the best of our knowledge, the solvent has not been used in [2,3]-Wittig rearrangement, probably because the rate of racemization of the carbanion has been thought to be much faster than that of the reaction with an electrophile at temperatures higher than its freezing point (11°C).
    • To the best of our knowledge, the solvent has not been used in [2,3]-Wittig rearrangement, probably because the rate of racemization of the carbanion has been thought to be much faster than that of the reaction with an electrophile at temperatures higher than its freezing point (11°C).
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    • 2.
    • 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.