Synthesis of (E)-1,4-bis(organyl) but-1-en-3-ynes by lithlium-tellurium exchange reaction on (Z)-1-butyltelluro-1,4-bis(organyl) but-1-en-3-ynes.

Dabdoub, Miguel J.; Dabdoub, Vânia B.; Comasseto, J. V.

doi:10.1016/s0040-4039(00)74184-0

Cited by 64 publications

(16 citation statements)

References 18 publications

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“…However, direct stereoselective synthesis of highly substituted conjugated enynes from 1,3-diynes is scarce. 17 To further demonstrate the synthetic utility of this protocol, we extended the iodosulfonylation reaction to 1,3-diynes. It was found that the reaction proceeded smoothly, and the polysubstituted conjugated enynes 7 were isolated in 48–74% yields when 1,3-diynes 6 reacted with 2 equiv of sodium sulfinates and 1.5 equiv of iodine in DCE/H 2 O (v:v = 2:1) at reflux (Table 4).…”

Section: Results and Discussionmentioning

confidence: 99%

Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates

et al. 2018

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An operationally simple, efficient, and metal-/peroxide-free three-component reaction of alkynes, iodine, and sodium sulfinates has been developed for the construction of highly functionalized tetrasubstituted alkenes. Iodo- and sulfonyl-containing tetrasubstituted alkenes, such as vinyl ketones, allylic alcohols, and conjugated enynes, could be obtained regio- and stereoselectively in up to 96% yield.

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Section: Results and Discussionmentioning

confidence: 99%

Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates

et al. 2018

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“…The key precursor in the synthesis of 3a is enyne 5a , from which the dibenzobarrelene skeleton is constructed by an intramolecular [4+2] cycloaddition reaction. Enyne 5a was obtained by nucleophilic substitution of 1‐lithiobut‐1‐en‐3‐yne 6 , generated by treatment of (butyltelluro)butenyne 7 with butyllithium in THF at –78 °C,, with 9‐(chloromethyl)anthracene ( 8a ). Subsequently, enyne 5a was heated at 60 °C in THF to furnish the desired 3a in 40 % yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Photophysical Properties of Dibenzobarrelene‐Incorporated 1,4‐Diphenyl‐1,3‐pentadienes and a 5‐Sila Derivative Having High Fluorescence Efficiency

et al. 2018

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Two dibenzobarrelene‐incorporated 1,3‐pentadienes and a 5‐sila derivative have been synthesized by intramolecular cycloaddition reactions between (9‐anthryl)methyl, (9‐anthryl)hydroxymethyl, or (9‐anthryl)dimethylsilyl groups and a phenylethynyl group linked by an ethene moiety with a cis conformation. The three compounds exhibit blue luminescence (λem = 432–445 nm) in CH2Cl2 with high quantum yields (ΦF = 0.83–0.92). In the solid state, the methylene and dimethylsilyl derivatives luminesce (λem = 442 and 438 nm, respectively) with narrow full‐width at half‐maxima (FWHM, 40 and 37 nm, respectively), whereas the hydroxymethylene compound shows a broad and slightly redshifted emission (λem = 488 nm, FWHM = 112 nm) due to intermolecular hydrogen bonding. The fluorescence intensity of the dimethylsilyl compound was decreased by desilylation with Bu4NF. The structures of the compounds were characterized unambiguously by NMR spectroscopy and X‐ray crystallography, and their photophysical properties were elucidated both experimentally as well as by TD‐DFT calculations.

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“…TLC plates were purchased from Merck (20 × 20 cm silica gel 60 F 254 ). [FcTeC(Fc)=C(H)C≡CFc] was prepared by following reported procedures …”

Section: Methodsmentioning

confidence: 99%

Synthetic and Structural Study on Orthometallated Ferrocene Complexes: Non‐Planar Metallabenzene and Five‐Membered Metallacycle Complexes with Closed Os₃ Triangles

Tauqeer

Singh

et al. 2018

Eur J Inorg Chem

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Thermolysis of (Z)-1-ferrocenyltelluro-1-ferrocenyl-4ferrocenyl-1-buten-3-yne with [Os 3 (CO) 12 ] in toluene gave two new clusters: non-planar six-membered metallacycle complex [Os 3 H(CO) 7 (μ 3 -Te){η 1 :η 1 :η 2 :η 2 -FcCCC(H)(Fc) 2 }] (1, Fc = ferrocenyl) and five-membered cyclometallated ring complex [Os 3 (CO) 7 -(μ 3 -Te){η 1 :η 1 :η 3 -FcC(H)C(H)CC(Fc) 2 }] (2). Compounds 1 and 2 may be thought to form by orthometallation of ferrocene with a closed Os 3 triangle by intramolecular rearrangement of atoms Scheme 1. Five-membered and six-membered ferrocenyl-substituted metallacycles.[a]

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Synthesis of (E)-1,4-bis(organyl) but-1-en-3-ynes by lithlium-tellurium exchange reaction on (Z)-1-butyltelluro-1,4-bis(organyl) but-1-en-3-ynes.

Cited by 64 publications

References 18 publications

Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates

Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates

Synthesis and Photophysical Properties of Dibenzobarrelene‐Incorporated 1,4‐Diphenyl‐1,3‐pentadienes and a 5‐Sila Derivative Having High Fluorescence Efficiency

Synthetic and Structural Study on Orthometallated Ferrocene Complexes: Non‐Planar Metallabenzene and Five‐Membered Metallacycle Complexes with Closed Os₃ Triangles

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Synthesis of (E)-1,4-bis(organyl) but-1-en-3-ynes by lithlium-tellurium exchange reaction on (Z)-1-butyltelluro-1,4-bis(organyl) but-1-en-3-ynes.

Cited by 64 publications

References 18 publications

Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates

Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates

Synthesis and Photophysical Properties of Dibenzobarrelene‐Incorporated 1,4‐Diphenyl‐1,3‐pentadienes and a 5‐Sila Derivative Having High Fluorescence Efficiency

Synthetic and Structural Study on Orthometallated Ferrocene Complexes: Non‐Planar Metallabenzene and Five‐Membered Metallacycle Complexes with Closed Os3 Triangles

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Synthetic and Structural Study on Orthometallated Ferrocene Complexes: Non‐Planar Metallabenzene and Five‐Membered Metallacycle Complexes with Closed Os₃ Triangles