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Volumn 55, Issue 41, 2016, Pages 12664-12667

Ethenesulfonyl Fluoride: The Most Perfect Michael Acceptor Ever Found?

Author keywords

electrophilic aromatic substitution; electrophilicity; linear free energy relationships; reaction kinetics; ylides

Indexed keywords

AROMATIC HYDROCARBONS; FLUORINE COMPOUNDS; FREE ENERGY;

EID: 84966667787     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201601875     Document Type: Article
Times cited : (87)

References (35)
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    • For a list of nucleophilicity parameters, N, s, and electrophilicity parameters, E, see
    • N and electrophilicity parameters E, see: http://www.cup.lmu.de/oc/mayr/DBintro.html.
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    • For other mechanistic studies of sulfonium ylides, see
    • For other mechanistic studies of sulfonium ylides, see:
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    • The configuration of 4 b was determined by crystallography; see the Supporting Information
    • The configuration of 4 b was determined by crystallography; see the Supporting Information.
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    • Analogous syntheses of indolizines have recently been described; see
    • Analogous syntheses of indolizines have recently been described; see: D. S. Allgäuer, H. Mayr, Eur. J. Org. Chem. 2013, 6379–6388.
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    • For the reasons discussed in the text, the rate constant for 3 b (open circle) was not used for the correlation. Although the slope of this correlation was fixed at 1.0 [to apply Eq. (1)], Figure 3 shows an excellent fit of the experimental data to the correlation line calculated with this constraint
    • For the reasons discussed in the text, the rate constant for 3 b (open circle) was not used for the correlation. Although the slope of this correlation was fixed at 1.0 [to apply Eq. (1)], Figure 3 shows an excellent fit of the experimental data to the correlation line calculated with this constraint.
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    • However, indole 9 e was obtained in 34, and TsOH (10 mol, in acetonitrile at 80 °C for 24 h, See the Supporting Information
    • However, indole 9 e was obtained in 34 % yield when 8 e was heated with 1 (1.5 equiv) and TsOH (10 mol %) in acetonitrile at 80 °C for 24 h. See the Supporting Information.


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