Hydrolithiation of .alpha.-olefins by a regiospecific two-step process. Transformation of alkyl phenyl sulfides to alkyllithium reagents

Screttas, Constantinos G.; Micha-Screttas, Maria

doi:10.1021/jo00400a008

Cited by 188 publications

(46 citation statements)

References 1 publication

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“…l mmHg (lit. 15 188-189°Cjl5 mmHg), nb 5 = 1.6060, Swt¾ = Figure 3. 1 H NMR spectra of (a) the adduct of thiophenol to styrene and of (b) the polymer of BDT to DVB 7 in CDCl3 (JEOL JMS-FX90Q).…”

Section: Preparation Of Addition Product Of Thiophenol and Styrenementioning

confidence: 97%

Polyaddition of Dithiol Compounds to Divinyl Compounds: The Kinetics of the Model Addition Reaction of Thiophenols to Styrenes

Kobayashi

Obata

Aoshima

et al. 1990

Polym J

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ABSTRACT:The addition reaction mechanism of thiophenol with styrene was studied as a model of the polyaddition of 1,4-benzenedithiol to 1,4-divinylbenzene. The addition reaction of thiophenol to styrene occurred without a side reaction and an adduct of the anti-Markownikoff's structure (SCH 2CH 2 ) was quantitatively obtained. The kinetic study shows that the rate-determining step of the addition reaction is the chain transfer reaction between thiophenol and P-phenylthiostyryl radical. The substituent effect of the chain transfer reaction was determined on various thiophenols and styrenes. Fairly good linear correlation was obtained for the Hammett plot of logk" to u+ on both monomers (p(k1r(St))= -0.60, p(k,,(TP)}= +0.64). These results are discussed in detail by comparing with polyaddition.

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Section: Preparation Of Addition Product Of Thiophenol and Styrenementioning

confidence: 97%

Polyaddition of Dithiol Compounds to Divinyl Compounds: The Kinetics of the Model Addition Reaction of Thiophenols to Styrenes

Kobayashi

Obata

Aoshima

et al. 1990

Polym J

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“…Data were corrected for absorption using the SADABS program and ω-scan technique was used for data collection [8,9]. The structures were solved by SIR97 [10] and were refined by full matrix least squares with SHELXL-97 [11].…”

Section: Methodsmentioning

confidence: 99%

“…Lewis acids serve as a catalyst for the methylene group inclusion reaction of thiols. Reactions of thiols with dimethoxymethane in the presence of four equivalents of Lewis acids, such as AlCl 3 , TiCl 4 and SnCl 4 were investigated [6][7][8][9][10][11][12]. Aluminum hydrogen sulfate acts as a catalyst for the efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones via the condensation of aromatic aldehydes, β-keto esters and urea (or thiourea) in methanol under solvent-free conditions [13].…”

Section: Introductionmentioning

confidence: 99%

Anhydrous Aluminum Chloride Catalyzed Methylene Group Inclusion: Mechanistic, Spectral and Single Crystal X-Ray Structural Study on Methanediyl Bis(Cyclohexylmethylcarbamodithioate)

Ramalingam

Rizzoli

Sivagurunathan³

et al. 2016

ILCPA

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In this study anhydrous AlCl3is used as a catalyst for the inclusion of a methylene group in to cyclohexylmethyldithiocarbamic acid to form methanediyl bis(cyclohexylmethylcarbamodithioate). Dichloromethane is used as a methylene group bearer in the reaction. A suitable mechanistic pathway involving+CH2Cl is discussed. FTIR, NMR and Mass spectral techniques have been used in the analysis. Single crystal X-ray structure of the compound was determined. FTIR spectrum of the compound showed υc-sband at 1073 cm-1and υC-Hvibrations appeared at 2853 and 2928 cm-1. Thioureide stretching band was observed at 1473 cm-1. The molecular ion peak in the Mass spectroscopy confirmed the proposed formula. H1NMR spectrum of the compound showed a signal at 4.33(s) ppm for α-CH of the cyclohexyl ring and -CH3protonsattached to nitrogen appeared at 3.40 ppm. Methylene proton (S-CH2-S) signal appeared at 3.16 ppm which is largely deshielded by the presence of two electronegative sulphur atoms on either side. The characteristic methylene carbon (S-CH2-S) signal appeared at 45.46 ppm in the13C NMR spectrum. Single crystal X-ray structural analysis of the compound showed it to be monomeric. Methylene carbon in S-CH2-S, C(9) is tetrahedrally bonded to two hydrogen atoms and two sulphur atoms S(2), S(3). The molecule stacks its cyclohexyl rings along ‘c’ axis of the unit cell. Short contacts in the form of supramolecular interactions such as C---S and S---S exist in the solid state at 3.49 and 3.50 Å respectively.

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“…A mixture of 513 mg (4 mmol) of naphthalene and 28 mg (4 mmol) of lithium in 5 mL of THF was stirred for 6 hours under argon [12]. The resulting deep-green mixture was cooled to ‫87מ‬ЊC.…”

Section: Reduction Of the Inner Salt 1 With Lithium Naphthalenide; 1mentioning

confidence: 99%

Oxidation and reduction of 2,2-bis(diethylamino)-2-ethylium-1-dithioate

et al. 1998

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Hydrolithiation of .alpha.-olefins by a regiospecific two-step process. Transformation of alkyl phenyl sulfides to alkyllithium reagents

Cited by 188 publications

References 1 publication

Polyaddition of Dithiol Compounds to Divinyl Compounds: The Kinetics of the Model Addition Reaction of Thiophenols to Styrenes

Polyaddition of Dithiol Compounds to Divinyl Compounds: The Kinetics of the Model Addition Reaction of Thiophenols to Styrenes

Anhydrous Aluminum Chloride Catalyzed Methylene Group Inclusion: Mechanistic, Spectral and Single Crystal X-Ray Structural Study on Methanediyl Bis(Cyclohexylmethylcarbamodithioate)

Oxidation and reduction of 2,2-bis(diethylamino)-2-ethylium-1-dithioate

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