A Convenient Method for the Introduction of a Vinylthio Group

Verboom, W.; Meijer, J.; Брандсма, Л.

doi:10.1055/s-1978-24813

Cited by 21 publications

(7 citation statements)

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“…The aryl vinyl sulfides were prepared by a modification of a literature procedure 11 with the exception of phenyl vinyl sulfide, which was obtained from Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Convenient criterion for the distinction between electrophilic and electron transfer reactions of electron-rich alkenes

Bauld

Aplin

Yueh

et al. 1998

J. Phys. Org. Chem.

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Both experimental and theoretical studies confirm that the formation of aryl vinyl ether and aryl vinyl sulfide cation radicals from the corresponding neutral substrates correlates with the Brown ' parameters as opposed to Hammett ' values. Peak oxidation potentials for both classes of substrates correlate preferentially with ' , as do gas-phase ionization energies calculated by both semi-empirical and ab initio methods. In contrast, the protonation energies of the same substrates, which relate to carbocation formation, correlate preferentially with ' values, as do rates of protonation and other electrophilic additions. These observations permit a sharp distinction between electrophilic and electron transfer reactions of these two common classes of electron-rich substrates. Using this criterion, the cycloadditions of tetracyanoethylene to these substrates are found to proceed via an electrophilic mechanism, rather than by a previously proposed electron transfer mechanism.

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“…The aryl vinyl sulfides were prepared by a modification of a literature procedure 11 with the exception of phenyl vinyl sulfide, which was obtained from Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Convenient criterion for the distinction between electrophilic and electron transfer reactions of electron-rich alkenes

Bauld

Aplin

Yueh

et al. 1998

J. Phys. Org. Chem.

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“…IR (KBr): 1593, 2165 cm -1 . 1 H NMR (400 MHz, CDCl 3 ): d (E form) = 0.92 (t, J = 7.3 Hz, 3 H), 1.44 (sext, J = 7.3 Hz, 2 H), 2.13 (dq, J = 7.3, 1.2 Hz, 2 H), 5.87 (dt, J = 14.7, 1.2 Hz, 1 H), 5.99 (dt, J = 14.7, 6.8 Hz, 1 H), 7.28-7.31 (m, 3 H), 7.40-7.47 (m, 2 H); d (Z form) = 0.94 (t, J = 7.3 Hz, 3 H), 1.45 (sext, J = 7.3 Hz, 2 H), 2.12 (dq, J = 7.3, 1.4 Hz, 2 H), 5.75 (dt, J = 9.0, 7.3 Hz, 1 H), 6.12 (dt, J = 9.0, 1.4 Hz, 1 H), 7.28-7.31 (m, 3 H), 7.40-7.47 (m, 2 H), 13 C NMR (100 MHz, CDCl 3 ): d (E + Z form) = 13.5, 13.6, 21.9, 22.1, 30.6, 34.7, 76.1, 77.7, 92.9, 96.7, 117.3, 121.8, 123.0, 123.1, 128.2, 128.2, 128.3, 128.3, 131.4, 131.5, 132.7, 132.9 8, 93.8, 121.9, 123.8, 127.0, 127.6, 128.1, 128.3, 128.3, 128.3, 128.5, 129.5, 131.5, 137.9, 140.4, 141.9. MS (EI): m/z (%) = 312 (57, M + ).…”

Section: Pent-1-enyl Phenylethynyl Sulfide (3f)mentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ): d = 6.89 (d, J = 15.4 Hz, 1 H), 7.01 (d,J = 15.4 Hz,1 H),8 H), 7.48-7.50 (m, 2 H). 13 C NMR (100 MHz, CDCl 3 ): d = 67. 8, 103.5, 115.1, 123.0, 126.1, 127.7, 128.3, 128.5, 128.6, 131.6, 133.6, 136.5 2, 68.3, 102.9, 112.0, 114.1, 123.1, 127.4, 128.3, 128.4, 129.4, 131.6, 133.7, 159.4 2, 68.1, 103.2, 113.7, 123.1, 126.1, 128.3, 128.5, 129.3, 129.3, 131.6, 133.7, 137.7…”

Section: Phenylethynyl Styryl Selenide (4a)mentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ): d = 6.88 (d, J = 15.3 Hz, 1 H), 6.95 (d, J = 15.3 Hz, 1 H), 7.24 (d, J = 8.3 Hz, 2 H), 7.28 (d, J = 8.3 Hz, 2 H), 7.32-7.34 (m, 3 H), 7.48-7.51 (m, 2 H). 13 C NMR (100 MHz, CDCl 3 ): d = 67.4, 103.9, 116.0, 122.9, 127.3, 128.4, 128.7, 128.8, 131.7, 132.0, 133.4, 135. Anal. Calcd for C 16 H 11 ClSe: C,60.49;H,3.49.…”

Section: -Chlorostyryl Phenylethynyl Selenide (4d)mentioning

confidence: 99%

“…Except for alkynyl vinyl sulfides, alkynyl vinyl chalcogenides constitute a nearly unexplored class of unsaturated chalcogenides. [11][12][13] Their preparation include multistep sequences employing aldehydes or 2-chloroethyl thiocyanate 13 and the reaction of lithium acetylides with b-chlorovinyl sulfenamides. 11 The sulfur derivatives, as the corresponding sulfoxides and sulfones, were convert-ed into sulfur, selenium, or nitrogen heterocycles by reaction with sodium sulfide, sodium selenide, or methylamine.…”

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confidence: 99%

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Stereoselective Synthesis of Alkynyl Vinyl Chalcogenides via Horner-Wittig Reaction

Silveira¹,

Rinaldi²,

Guadagnin³

et al. 2009

Synthesis

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New (diphenylphosphoryl)methyl phenylethynyl sulfides, selenides, or tellurides were prepared by the reaction of (diphenylphosphoryl)methyl p-toluenesulfonate with alkynethiols, -selenols, or -tellurols at room temperature. The (diphenylphosphoryl)methyl phenylethynyl sulfides, selenides, or tellurides reacted with aldehydes and cyclic ketones to give the corresponding alkynyl vinyl sulfides, selenides, or tellurides, with preferential E-stereochemistry, in a Horner-Wittig-type reaction.Organochalcogenium compounds have become the key component of a variety of versatile and useful reagents for organic synthesis. The multiple applications of organochalcogenium chemistry have been well described in a number of review articles 1 and books. 2 Functionalized alkynyl 3 and alkenyl 4 chalcogenides have a great potential in organic synthesis, since they are valuable intermediates for the selective preparation of several organic compounds. Furthermore, methods for the synthesis of chalcogeno-substituted acetylenes have also been described in recent years, 3,5 although in a reduced number compared to their vinylic counterparts. The most common approach to alkynyl chalcogenides employs the reaction of a metal alkynide with elemental chalcogenium followed by reaction with an alkyl halide or an appropriate electrophilic reagent. 5aAmong the many applications of vinyl selenides, divinyl selenides, and vinyl sulfides, the cross-coupling reaction with Grignard reagents catalyzed by nickel 6 and palladium 7 to give the corresponding cross-coupled products, has been described. On the other hand, palladium-4a,8 and nickel-catalyzed 6a,9 cross-coupling reactions and tellurium-metal exchange reactions 10 demonstrate the usefulness of vinyl tellurides.Except for alkynyl vinyl sulfides, alkynyl vinyl chalcogenides constitute a nearly unexplored class of unsaturated chalcogenides. 11-13 Their preparation include multistep sequences employing aldehydes or 2-chloroethyl thiocyanate 13 and the reaction of lithium acetylides with b-chlorovinyl sulfenamides. 11 The sulfur derivatives, as the corresponding sulfoxides and sulfones, were converted into sulfur, selenium, or nitrogen heterocycles by reaction with sodium sulfide, sodium selenide, or methylamine. 14 Alkynyl vinyl sulfides were also claimed to have pesticide and bactericide activity. 15In light of the above comments and from our continuous interest in the development of new vinyl chalcogenides based on Horner-Wittig reaction, 16 we became interested in the development of practical stereoselective synthetic methods for alkynyl vinyl chalcogenides. For instance, we have recently described a detailed study of the synthesis of symmetrical and unsymmetrical divinyl sulfides, selenides, and tellurides from chalcogenyl phosphonates and phosphine oxides, by reaction with arylaldehydes and cyclic ketones. 17 Thus, as a continuation of this study, we planned the preparation of alkynyl vinyl sulfides, selenides, and tellurides by a similar route, starting from (diphenylphosphoryl)methyl phenyl...

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Lithium (Trimethylsilyl)acetylide

Fuhry

2001

Encyclopedia of Reagents for Organic Synthesis

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A Convenient Method for the Introduction of a Vinylthio Group

Cited by 21 publications

References 0 publications

Convenient criterion for the distinction between electrophilic and electron transfer reactions of electron-rich alkenes

Convenient criterion for the distinction between electrophilic and electron transfer reactions of electron-rich alkenes

Stereoselective Synthesis of Alkynyl Vinyl Chalcogenides via Horner-Wittig Reaction

Lithium (Trimethylsilyl)acetylide

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