Cyclic Sulfones. II. The Polymerization of Styrene in the Presence of 3,4-Diphenylthiophene-1-dioxide and 3,4-Di-(ρ-chlorophenyl)-thiophene-1-dioxide<sup>1</sup>

Overberger, C. G.; Mallon, H.‐J.; Fine, Ralph

doi:10.1021/ja01167a034

Cited by 22 publications

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“…It is known that the electron density of the C–C triple bond of a propiolic acid is weaker as compared to that of an acetylene, due to the electron-withdrawing nature of the carboxyl group. Thus, as the Cu center of the catalytic species approached the triple bond, the nucleophilic attack of the thiyl anion was induced . The reductive C–S coupling to form a cyclic alkene/carboxylate copper complex intermediate 3 was the key step determining the stereoselectivity.…”

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confidence: 99%

Carbon Dioxide Mediated Stereoselective Copper-Catalyzed Reductive Coupling of Alkynes and Thiols

2012

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A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO(2) atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO(2) atmosphere. The reaction system is robust and utilizes inexpensive, readily available substrates. A cyclic alkene/carboxylate copper complex intermediate is proposed as the key step in determining the stereoselectivity, and an equivalent amount of water is found to play an active role as a proton donor.

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confidence: 99%

Carbon Dioxide Mediated Stereoselective Copper-Catalyzed Reductive Coupling of Alkynes and Thiols

2012

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“…Synthetic pathway to 2‐thia‐dibenzo[ e , h ]azulene scaffold follows known synthesis of 3,4‐diarylthiophenes (Scheme 3) [23–25]. Starting ketones 1a , 1b , 1c are oxidized with selenium dioxide to corresponding 1,2‐diketones 4a , 4b , 4c , which are condensed with dimethyl 2,2′‐thiodiacetate in the presence of potassium tert ‐butoxide in tert ‐butanol.…”

Section: Synthetic Pathways To Dibenzo[eh]azulenesmentioning

confidence: 99%

Dibenzo[b,f]oxepin‐10(11H)‐one and dibenzo[b,f]thiepin‐10(11H)‐one as useful synthons in the synthesis of various dibenzo[e,h]azulenes

Pešić

Landek

Rupčić

et al. 2011

Journal of Heterocyclic Chem

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The present review focuses on dibenzo[b,f]oxepin‐10(11H)‐one (I, X = O) and dibenzo[b,f]thiepin‐10(11H)‐one (I, X = S) as common synthons in the efficient synthesis of various dibenzoxepino[4,5‐ and dibenzothiepino[4,5]‐fused five‐membered heterocycles: [2,3] fused thiophene (II), [3,4] fused thiophene (III), furan (IV), pyrrole (V), imidazole (VI), pyrazole (VII), oxazole (VIII), and thiazole (IX). The potential of I to be converted into reactive intermediates that readily undergo heteroaromatic annulation reactions by cyclocondensation with proper binucleophiles allows formation of a range of enumerated functionalized dibenzo[e,h]azulene [4] structures (II, III, IV, V, VI, VII, VIII, IX). Dibenzo[e,h]azulenes as heterotetracyclic scaffold can be exploited in further modifications to obtain compounds with altered physicochemical and biological profile. J. Heterocyclic Chem., (2012).

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“…The separated organic layer was dried over anhydrous MgSO 4 and evaporated to give 1 as yellow liquid (7.07 g, 62% yield). [49] 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 4.05 (q, J = 6.8 Hz, Sodium metal (2.4 g, 0.21 mol) was dissolved in ethanol (75 mL) and the solution was added dropwise to a mixture of 1 (2.00 g, 0.010 mol) and diethyl oxalate (4.5 g, 0.03 mol) for 30 min in ice bath. The reaction was refluxed under nitrogen atmosphere for 3 h. Then the reaction was cooled to room temperature, added water (400 mL), and acidified by conc.…”

Section: Diethyl Thiodiglycolate (1)mentioning

confidence: 99%

Direct Arylation Polymerization Of 2?-Octyl-3,4-Ethylenedioxythiophene For Donor-Acceptor Conjugated Copolymer Synthesis

Tiyasakulchai

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Direct arylation polymerization (DArP) is a new palladium-catalyzed cross-coupling method to synthesize conjugated copolymers. This reaction can generate C-C bonds between simple arenes and dibromoarenes, without passing through organometallic intermediates. In this work, we synthesized new donor-acceptor conjugated copolymers based on 2?-octyl-3,4-ethylenedioxythiophene (OEDOT) donor coupled with 3,5-dibromo-1,2,4-triazole, 4,7-dibromo-2,1,3-benzothiadiazole, 4,7-dibromo-5,6-difluoro-2,1,3-benzothiadiazole, 4,7-dibromo-1,2,3-benzotriazole, 4,7-dibromo-2-octyl-1,2,3-benzotriazole, 1,4-dibromo-2,5-(tert-butyldimethylsilanyl oxy)benzene, 5,7-dibromothieno[3,4-b]pyrazine and 5,7-dibromo-2,3-diphenyl thieno[3,4-b]pyrazine to become polymers P1-6 and P9-10, respectively in various range of yields of 16-88%. Polymer P7 was prepared from deprotection followed by oxidation of polymer P6. These copolymers exhibited various UV-Visible absorptions with ?max values ranging from 328 to 958 nm.

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Cyclic Sulfones. II. The Polymerization of Styrene in the Presence of 3,4-Diphenylthiophene-1-dioxide and 3,4-Di-(ρ-chlorophenyl)-thiophene-1-dioxide¹

Cited by 22 publications

References 1 publication

Carbon Dioxide Mediated Stereoselective Copper-Catalyzed Reductive Coupling of Alkynes and Thiols

Carbon Dioxide Mediated Stereoselective Copper-Catalyzed Reductive Coupling of Alkynes and Thiols

Dibenzo[b,f]oxepin‐10(11H)‐one and dibenzo[b,f]thiepin‐10(11H)‐one as useful synthons in the synthesis of various dibenzo[e,h]azulenes

Direct Arylation Polymerization Of 2?-Octyl-3,4-Ethylenedioxythiophene For Donor-Acceptor Conjugated Copolymer Synthesis

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Cyclic Sulfones. II. The Polymerization of Styrene in the Presence of 3,4-Diphenylthiophene-1-dioxide and 3,4-Di-(ρ-chlorophenyl)-thiophene-1-dioxide1

Cited by 22 publications

References 1 publication

Carbon Dioxide Mediated Stereoselective Copper-Catalyzed Reductive Coupling of Alkynes and Thiols

Carbon Dioxide Mediated Stereoselective Copper-Catalyzed Reductive Coupling of Alkynes and Thiols

Dibenzo[b,f]oxepin‐10(11H)‐one and dibenzo[b,f]thiepin‐10(11H)‐one as useful synthons in the synthesis of various dibenzo[e,h]azulenes

Direct Arylation Polymerization Of 2?-Octyl-3,4-Ethylenedioxythiophene For Donor-Acceptor Conjugated Copolymer Synthesis

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Cyclic Sulfones. II. The Polymerization of Styrene in the Presence of 3,4-Diphenylthiophene-1-dioxide and 3,4-Di-(ρ-chlorophenyl)-thiophene-1-dioxide¹