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Volumn 105, Issue 6, 1983, Pages 1598-1608

Tris(dialkylamino)sulfonium Enolates. Synthesis, Structure, and Reactions1’

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EID: 0000923060     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00344a030     Document Type: Article
Times cited : (246)

References (55)
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    • Disadvantages include the high cost and the suscepttbility of the TAS moiety to a base-promoted fragmentation
    • Disadvantages include the high cost and the suscepttbility of the TAS moiety to a base-promoted fragmentation.
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    • Some concentration dependency was observed. However, further precise measurements at lower concentration were not made because of the moisture and air sensitivity of 5
    • Some concentration dependency was observed. However, further precise measurements at lower concentration were not made because of the moisture and air sensitivity of 5.
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    • Since ‘H NMR spectra of phenol and phenyl trimethylsilyl ether exhibit similar signal patterns in the aromatic region, use of the enol silyl ether as a neutral model compound would not be unreasonable
    • Since ‘H NMR spectra of phenol and phenyl trimethylsilyl ether exhibit similar signal patterns in the aromatic region, use of the enol silyl ether as a neutral model compound would not be unreasonable.
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    • Planar structures are assumed for the models 6 and 7, although for the actual compounds 1 and 5 two ortho and meta positions are equivalent in the NMR time scale. The structures for the calculations are derived by using optimized bond lengths
    • Planar structures are assumed for the models 6 and 7, although for the actual compounds 1 and 5 two ortho and meta positions are equivalent in the NMR time scale. The structures for the calculations are derived by using optimized bond lengths (MINDO/3) for vinyloxy anion (1.374 A for C-C and 1.257 A for C-O) and standard parameters for other fragments: Baird, N.C.; Dewar, M.J.S.J. Chem. Phys. 1969, 50, 1262. Bingham, R.C.; Dewar, M.J.S.; Lo, D.H.J. Am. Chem. Soc. 1975, 97, 1285.
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    • This may be due to magnetic anisotropy of the oxygen atom
    • This may be due to magnetic anisotropy of the oxygen atom.
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    • Change in electron distribution is not the sole factor controlling the magnitude of the chemical shift change. The chemical shift for charged species is highly dependent on the nature of substituents, particularly heteroatoms
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    • For the quaternary ammonium fluoride promoted reaction, see ref 6.
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    • For the quaternary ammonium fluoride catalyzed aldol reaction, see
    • For the quaternary ammonium fluoride catalyzed aldol reaction, see ref 7.
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    • This result is to be compared with the corresponding reaction of the zinc enolate that gives ca. 40% of the equatorial isomers3
    • This result is to be compared with the corresponding reaction of the zinc enolate that gives ca. 40% of the equatorial isomers3
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    • Organic Syntheses
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.