The reaction of diorganyl diselenides and ditellurides with organic mercury compounds. A convinient method for the synthesis of unsymmetrical organic selenides and tellurides

Okamoto, Yoshiyuki; Yano, Takefumi

doi:10.1016/s0022-328x(00)87494-x

Cited by 65 publications

(13 citation statements)

References 8 publications

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“…Okamoto and Yano have obtained this compound at room temperature by a similar method but using dioxane as solvent [9]. We have, however, observed that the use of boiling xylene improves the yield and the isolation process.…”

Section: Resultsmentioning

confidence: 97%

Benzeneselenolates of Mercury(II). Crystal and Molecular Structures of [Hg(SePh)2] and (Bu4N)[Hg(SePh)3]

Lang

Dias

Abram

et al. 2000

Z. anorg. allg. Chem.

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The reaction of dibenzenediselenide, (SePh)2, with mercury in refluxing xylene gives bis(benzeneselenolato)mercury(II), [Hg(SePh)2], in a good yield. (nBu4N)[Hg(SePh)3] is obtained by the reaction of [Hg(SePh)2] with a solution of [SePh]– and (nBu4N)Br in ethanol. The solid state structures of both compounds have been determined by X‐ray diffraction. The mercury atom in [Hg(SePh)2] (space group C2, a = 7.428(2), b = 5.670(1), c = 14.796(4) Å, β = 103.60(1)°) is linearly co‐ordinated by two selenium atoms (Hg–Se = 2.471(2) Å, Se–Hg–Se = 178.0(3)°). Additional weak interactions between the metal and selenium atoms of neighbouring molecules (Hg…Se = 3.4–3.6 Å) associate the [Hg(SePh)2] units to layers. The crystal structure of (nBu4N)[Hg(SePh)3] (space group P21/c, a = 9.741(1), b = 17.334(1), c = 21.785(1) Å, β = 95.27(5)°) consists of discrete complex anions and (nBu4N)+ counter ions. The coordination geometry of mercury is distorted trigonal‐planar with Hg–Se distances ranging between 2.5 and 2.6 Å.

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Section: Resultsmentioning

confidence: 97%

Benzeneselenolates of Mercury(II). Crystal and Molecular Structures of [Hg(SePh)2] and (Bu4N)[Hg(SePh)3]

Lang

Dias

Abram

et al. 2000

Z. anorg. allg. Chem.

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“…Satisfactory results, however, were only achieved by combining both. The mechanism of ring closure remains speculative, but the one proposed in Figure 3 is based on literature reports that mercury inserts into the Te-Te bond, generating species of type RTe-Hg-TeR [19][20]. It is probable that this initial insertion is followed by an intramolecular nucleophilic attack targeting the thiocarbonyl moiety and subsequent reductive desulfurization.…”

Section: Resultsmentioning

confidence: 99%

Organotellurium Chemistry: Synthesis and Properties of 2-Acylamino- and 2-Arylamino-1,3-benzotellurazoles

Smith¹,

Franklin²,

Goutierrez³

et al. 2019

AJHC

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Synthetic methods have been developed to prepare novel 1,3-benzotellurazoles carrying acylamino and arylamino moieties in position 2, in order to investigate their propensity to self-assemble to supramolecular structures. The targeted compounds were obtained in yields ranging from 44% to 67%, by reacting bis(2-aminophenyl) ditelluride with acyl-and aryl isothiocyanates, respectively, and subsequent reductive cyclization of the resulting thiourea derivatives. Seven novel 1,3benzotellurazole derivatives were prepared: 2-benzoylamino-1,3-benzotellurazole, 2-(4-chlorobenzoylamino)-1,3benzotellurazole, 2-(2-bromobenzoylamino)-1,3-benzotellurazole, 2-(4-bromobenzoylamino)-1,3-benzotellurazole, 2-(4methoxybenzoylamino)-1,3-benzotellurazole, 2-phenylamino-1,3-benzotellurazole, and 2-(4-chlorophenylamino-1,3benzotellurazole. A simplified protocol was employed to synthesize all acyl isothiocyanates needed for their preparation from benzoyl halide derivatives and potassium thiocyanate. The reductive cyclization of the intermediate thioureas was challenging, only the use of hydroxymethanesulfinate in the presence of elemental mercury provided synthetically useful product yields. A mechanism was proposed, consisting of the insertion of mercury into the Te-Te bond, followed by intramolecular nucleophilic attack of the thiocarbonyl moiety by the resulting insertion product. All 2-acylamino-1,3-benzotellurazoles are crystalline solids, which are stable to ambient light, air and moderate heat. A characterization of selected samples by X-ray crystallography indicated that they form dimers in solid state, resulting from hydrogen bonding between the exocyclic and endocyclic nitrogen atoms of two adjacent molecules. This sets them apart from 2-alkyl-and 2-aryl-1,3-benzotellurazoles, which are known to self-assemble into supramolecular wires.

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“…Following ref. 15, an attempt was made to synthesize Hg(SeMe);! by stirring Me2Se2 and Hg in benzene at room temperature.…”

Section: Methodsmentioning

confidence: 99%

A multinuclear (¹³C, ³¹P, ⁷⁷Se, ¹²⁵Te, ¹⁹⁹Hg) magnetic resonance study of the adamantane-like clusters [(μ-ER)₆(HgE′PR′₃)₄]²⁺ (E = S, Se, Te; E′ = S, Se; R′ = Ph, c-C₆H₁₁) and the precursors [Hg(E′PR′₃)_n]²⁺¹⁻³

Dean¹,

Manivannan²

1990

Can. J. Chem.

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PHILIP A. W. DEAN and VEERAGATHY MANIVANNAN. Can. J. Chem. 68,214 (1990). The cations [Hg(~'~R'3),]2+ (E' = S or Se; R' = C-C6HI I , n = 2-4; R' = Ph, n = 3 or 4) are obtained in solution from the new salts [Hg(E'PR'3)n](C104)2 (El = S or Se; n = 2, R' = C-C6HII; n = 3, R' = Ph) and their stoichiometric mixtures with EfPRI3. They have been characterized at reduced temperature using multinuclear (I3C, 3 1~, 77Se (where appropriate), and ' 9 9~g ) NMR. Cations of the type [(p-ER)6(HgE'PR'3)4]2+ (ER = S alkyl, SePh, or TePh, but not SPh), prepared cleanly in solution from Hg (ER).,, [Hg(E'PR'3n](C104)2r and E'PRf3 in the correct stoichiometric ratio, have been characterized in the same manner, and shown to possess an adamantanoid structure. The product with ER = TePh, E'PRr3 = SPPh3 has been isolated analytically pure. These tetranuclear cations are the first discrete species containing the adamantanoid skeleton (F-ER)'(H~E')~ (E, E' = chalcogen). At reduced temperature, inversion at E is slow on the NMR time scale for ER = TePh. Under these conditions, the TePh-bridged cations occur predominantly as an isomer of CI symmetry for E'PRr3 = SPPh3, SPCy3, SePPh3. However, the SePCy3 analogue appears to exist as an equilibrium mixture of an isomer of CI symmetry and an isomer of C3 symmetry. Ligand Chem. 68, 214 (1990). On a obtenu les cations [Hg(E'PR'3),]2+ (E' = S ou Se; R' = c-C6Hll, n = 2-4; R' = Ph, n = 3 ou 4) en solution en faisant rCagir les nouveaux sels [Hg(E'PR'3),](C104)2 (E' = S ou Se; n = 2, R' = c-C6HII; n = 3, R' = Ph) ainsi que leurs melanges stoechiomCtriques avec du E1PRI3. On les a caractCrisCs B basse tempkrature en faisant appel B la RMN multinuclCaire (I3C, 31P, 77Se (lorsqu7appropriC) et 1 9 9~g ) . On peut priparer trks proprement des solutions des cations du type [ (~-E R )~[ H~( E ' P R '~)~]~+ (ER

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The reaction of diorganyl diselenides and ditellurides with organic mercury compounds. A convinient method for the synthesis of unsymmetrical organic selenides and tellurides

Cited by 65 publications

References 8 publications

Benzeneselenolates of Mercury(II). Crystal and Molecular Structures of [Hg(SePh)2] and (Bu4N)[Hg(SePh)3]

Benzeneselenolates of Mercury(II). Crystal and Molecular Structures of [Hg(SePh)2] and (Bu4N)[Hg(SePh)3]

Organotellurium Chemistry: Synthesis and Properties of 2-Acylamino- and 2-Arylamino-1,3-benzotellurazoles

A multinuclear (¹³C, ³¹P, ⁷⁷Se, ¹²⁵Te, ¹⁹⁹Hg) magnetic resonance study of the adamantane-like clusters [(μ-ER)₆(HgE′PR′₃)₄]²⁺ (E = S, Se, Te; E′ = S, Se; R′ = Ph, c-C₆H₁₁) and the precursors [Hg(E′PR′₃)_n]²⁺¹⁻³

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The reaction of diorganyl diselenides and ditellurides with organic mercury compounds. A convinient method for the synthesis of unsymmetrical organic selenides and tellurides

Cited by 65 publications

References 8 publications

Benzeneselenolates of Mercury(II). Crystal and Molecular Structures of [Hg(SePh)2] and (Bu4N)[Hg(SePh)3]

Benzeneselenolates of Mercury(II). Crystal and Molecular Structures of [Hg(SePh)2] and (Bu4N)[Hg(SePh)3]

Organotellurium Chemistry: Synthesis and Properties of 2-Acylamino- and 2-Arylamino-1,3-benzotellurazoles

A multinuclear (13C, 31P, 77Se, 125Te, 199Hg) magnetic resonance study of the adamantane-like clusters [(μ-ER)6(HgE′PR′3)4]2+ (E = S, Se, Te; E′ = S, Se; R′ = Ph, c-C6H11) and the precursors [Hg(E′PR′3)n]2+1−3

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A multinuclear (¹³C, ³¹P, ⁷⁷Se, ¹²⁵Te, ¹⁹⁹Hg) magnetic resonance study of the adamantane-like clusters [(μ-ER)₆(HgE′PR′₃)₄]²⁺ (E = S, Se, Te; E′ = S, Se; R′ = Ph, c-C₆H₁₁) and the precursors [Hg(E′PR′₃)_n]²⁺¹⁻³