(1 Z ,3 Z )-Buta-1,3-dienyl-1-lithium species and substituted tellurophenes by Te/Li exchange on (1 Z ,3 Z )-butyltelluro-1,3-butadienes and (1 Z ,3 Z )-1,4-bis(butyltelluro)-1,3-butadienes

Dabdoub, Miguel J.; Dabdoub, Vânia B.; Guerrero, Palimécio G.; Silveira, Cláudio C.

doi:10.1016/s0040-4020(97)00148-8

Cited by 39 publications

(17 citation statements)

References 80 publications

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“…2. 19 The analysis of the above result revealed that 5g adopt an 1,3-alternate conformation in the solid state. Porphyrinogen 5g has a Te/Te distance of 4.61 A and the two Te atoms occupy the same side of core and no ipped tellurophene was found in the crystal.…”

Section: Introductionmentioning

confidence: 87%

Synthesis of 5,10,15,20-meso-unsubstituted and 5,10,15,20-meso-substituted-21,23-ditellura/diselena core-modified porphyrinogens: oxidation and detection of mercury(ii)

et al. 2014

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Tellurium and selenium incorporated 5,10,15,20-meso-unsubstituted-21,23-ditellura/diselena coremodified porphyrinogens (N 2 Te 2 and N 2 Se 2 ), 5,10,15,20-meso-unsubstituted-21-tellura/selena coremodified porphyrinogens (N 3 Te and N 3 Se) and fully substituted meso-carbons porphyrinogens (N 2 Te 2 , N 2 Se 2 and higher analogs) are synthesized by 3 + 1 condensation of tellurophene/ selenophene dipyrranes and their corresponding diols in the presence of BF 3 -etharate or BF 3methanol. The meso-unsubstituted and substituted porphyrinogens were oxidized with chloranil/0.1% aqueous FeCl 3 in CHCl 3 at room temperature to obtain the corresponding porphines and porphyrins which are further reduced to corresponding chlorin and bacteriochlorin, whereas the fully mesosubstituted porphyrinogens were found to be good ligands for Hg 2+ . The structures of the products were characterized by IR, 1 H, 13 C, 125 Te, 77 Se NMR, CHN analysis, mass spectrometry and singlecrystal XRD.

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Section: Introductionmentioning

confidence: 87%

Synthesis of 5,10,15,20-meso-unsubstituted and 5,10,15,20-meso-substituted-21,23-ditellura/diselena core-modified porphyrinogens: oxidation and detection of mercury(ii)

et al. 2014

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“…Absorption corresponding to the carbonyl groups was not observed in the infrared spectrum, but a carbon−carbon triple bond was still present at 2184 cm -1 . The presence of a doublet at 8.93 ppm ( J = 6.9 Hz) and another one at 7.98 ppm ( J = 6.9 Hz) in the 1 H NMR spectrum indicated the presence of hydrogens with strong aromatic character, , probably bound to adjacent carbons. The two doublets that appear at 6.61 and 7.52 ppm showing a coupling constant of 10.4 Hz could be due to the presence of vinylic hydrogens bonded at one double bond of a cis configuration.…”

Section: Resultsmentioning

confidence: 98%

“…More recently, we observed that β-unsubstituted tellurophenes can be synthesized by a Te/Li exchange reaction on 1,4-bis(butyltelluro)-1,3-butadienes which were obtained from the corresponding 1,4-bis(butyltelluro)-1-buten-3-ynes …”

Section: Resultsmentioning

confidence: 99%

Unexpected Reaction of 1-Butyltelluro-4-phenyl-1-buten-3-yne under Rupe Reaction Conditions

et al. 1998

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Treatment of 1-butyltelluro-4-phenyl-1-buten-3-yne (3) with an aqueous solution of formic acid results in formation of the unexpected 2-phenyl-3-(4-phenylbut-3-yn-1-enyltelluro)tellurophene 5. Formation of the expected α,β-unsaturated ketone β-telluro-substituted 4 was not observed by the reaction of 3 under Rupe reaction conditions. The structure of the product obtained was confirmed by X-ray diffraction of the dichlorotelluro derivative 6.

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“…Furthermore, reaction of n-butyllithium with 1,4-bis(butyltelluro)-1,3-butadiene 109 did not afford the 1,4-dilithium species 110 as expected, rather, a ring closure to form tellurophene 111 was observed (Scheme 41). 65 The first tellurium-lithium exchange occurs, and before the second exchange takes place, the tellurium atom is intramolecularly attacked by the vinyl anion, and the aromatic heterocycle is formed. A second equivalent of n-butyllithium is assumed to deprotonate the a-position of tellurophene.…”

Section: Scheme 39 Scheme 40mentioning

confidence: 99%

New development of synthesis and reactivity of seleno- and tellurophenes

Rhoden

Zeni²

2011

Org. Biomol. Chem.

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(1 Z ,3 Z )-Buta-1,3-dienyl-1-lithium species and substituted tellurophenes by Te/Li exchange on (1 Z ,3 Z )-butyltelluro-1,3-butadienes and (1 Z ,3 Z )-1,4-bis(butyltelluro)-1,3-butadienes

Cited by 39 publications

References 80 publications

Synthesis of 5,10,15,20-meso-unsubstituted and 5,10,15,20-meso-substituted-21,23-ditellura/diselena core-modified porphyrinogens: oxidation and detection of mercury(ii)

Synthesis of 5,10,15,20-meso-unsubstituted and 5,10,15,20-meso-substituted-21,23-ditellura/diselena core-modified porphyrinogens: oxidation and detection of mercury(ii)

Unexpected Reaction of 1-Butyltelluro-4-phenyl-1-buten-3-yne under Rupe Reaction Conditions

New development of synthesis and reactivity of seleno- and tellurophenes

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