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PROTIODESILYLATION OF SUBSTITUTED 2-TRIMETHYLSILYLTHIOPHENS

DOI: 10.1039/P29810000931

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 931 - 934 (1981)

Update date:2022-08-11

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Authors:

Seconi, GiancarloSeconi, Giancarlo

Eaborn, ColinEaborn, Colin

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Article abstract of DOI:10.1039/P29810000931

First-order rate constats at 50 deg C have been determined for cleavage of the thiophen compounds XC4H2S<*>SiMe3-2 in mixtures of (a) MeOH (5 vol.) with aqueous HClO4 (2 vol.) and (b) CH3CO2H (4 vol.) with aqueous H2SO4 (3 vol.) Relative rates krel, in the first medium are (X =) 5-OMe, 7 200; 5-Me, 36; H, 1.00; 5-Cl, 1.08E-1; 5-Br, 9.0E-2; 3-Br, 5.0E-2; 4-Br, 4.9E-3, and in the second medium 5-Me, 36; H, 1.00; 5-Cl, 1.28E-1; 5-Br, 9.8E-2; 3-Br, 5.5E-2; 4-Br, 6.5E-3; 5-NO2, 9.1E-7; 3-NO2, 7.1E-7.Except for the nitro-compounds, the two sets of log krel values show excellent linear correlations with values for the corresponding XC6H4<*>SiMe3 compounds, with 3-, 4-, and 5-X in the thiophen ring being taken as equivalent to o-, m-, and p-X groups, respectively, in the benzene ring, the effects of substituents being a litle larger in the thiophen than the benzene system; 3- and 5-O2NC4H2S<*>SiMe3 are less reactive than would be expected from the correlations.Again with the exception of the data for the nitro-compound, the krel values for the 4- and 5- substituted thiophens show very good correlation with ?m+ and ?p+ constants.

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Product name:2-Bromothiophene

Cas No:1003-09-4

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