Reaktionen von 1,2‐Bis(trimethylsilyl)iminen mit Selen‐und Tellur‐halogeniden

Neidlein, R.; Knecht, Dagmar

doi:10.1002/hlca.19870700420

Cited by 14 publications

(3 citation statements)

References 12 publications

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“…[67] Scheme 46 Reaction of a 1,2-Bis[(trimethylsilyl)imine] with Selenium Oxychloride [67] N Se N This document was downloaded for personal use only. [67] Scheme 46 Reaction of a 1,2-Bis[(trimethylsilyl)imine] with Selenium Oxychloride [67] N Se N This document was downloaded for personal use only.…”

Section: Methods 4: Reaction Of 12-bis[(trimethylsilyl)imines] With Smentioning

confidence: 99%

“…3,4-Diphenyl-1,2,5-selenadiazole (75): [67] A soln of N,N¢-bis(trimethylsilyl)-1,2-diphenylethanediimine (76; 50 mg, 0.14 mmol) in dry toluene (5 mL 3-Phenyl-1,2,5-selenadiazole (78); Typical Procedure: [64] A soln of 1.5 M PhMgBr (3 equiv) in dry Et 2 O was stirred at -40 8C under N 2 while a 0.3 M soln of 1,2,5-thiadiazole (77; 1 equiv) in Et 2 O was added dropwise and the mixture stirred at -40 8C for 2 h. Then Se 2 Cl 2 (3.25 equiv), freshly prepared by heating SeCl 4 and Se (1:3), was added dropwise and the mixture allowed to warm to rt and stirred for 3 h. The mixture was treated with H 2 O (50 mL) and filtered to remove Se. The filtrate was saturated with (NH 4 ) 2 SO 4 and extracted with Et 2 O, then the Et 2 O extract was dried (Na 2 SO 4 ) and evaporated.…”

Section: Methods 4: Reaction Of 12-bis[(trimethylsilyl)imines] With Smentioning

confidence: 99%

“…After 2 h the soln was cooled to -60 8C and a soln of TeCl 4 (2.64 g, 9.8 mmol) in THF (20 mL) was added followed after several minutes by a soln of Et 3 N (15.2 g, 150 mmol) in THF (12 mL). [67] Scheme 67 Reaction of a 1,2-Bis[(trimethylsilyl)imine] with Tellurium Tetrachloride [67] 122 85% [67] A soln of TeCl 4 (405 mg, 1.5 mmol) in dry toluene (10 mL) was added dropwise to a soln of bis[(trimethylsilyl)imine] 100 (520 mg, 1.48 mmol) in dry toluene (20 mL) stirring at rt. The filtrate was retained and the solid extracted in a Soxhlet apparatus under N 2 with THF (150 mL).…”

Section: Methods 1: Nitrationmentioning

confidence: 99%

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Product Class 27: Selenazoles and Tellurazoles Containing One or More Other Heteroatoms

Storr¹,

Gilchrist²

2004

Category 2, Hetarenes and Related Ring Systems

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Section: Methods 4: Reaction Of 12-bis[(trimethylsilyl)imines] With Smentioning

confidence: 99%

Section: Methods 4: Reaction Of 12-bis[(trimethylsilyl)imines] With Smentioning

confidence: 99%

Section: Methods 1: Nitrationmentioning

confidence: 99%

See 1 more Smart Citation

Product Class 27: Selenazoles and Tellurazoles Containing One or More Other Heteroatoms

Storr¹,

Gilchrist²

2004

Category 2, Hetarenes and Related Ring Systems

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New Charge‐Transfer Complexes with 1,2,5‐Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction

Chulanova

Pritchina

Malaspina

et al. 2016

Chemistry A European J

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The design and synthesis of novel charge-transfer (CT) complexes are of interest for fundamental chemistry and applications to materials science. In addition to the recently described first CT complex with both electron acceptor (A) and donor (D) groups belonging to the 1,2,5-thiadiazole series (1; A: 4-nitro-2,1,3-benzothiadiazole; D: 4-amino-2,1,3-benzothiadiazole), herein novel CT complexes 2 and 3 with 1,2,5-thiadiazoles as both A (4,6-dinitro-2,1,3-benzothiadiazole and [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole) and D (4-amino-2,1,3-benzothiadiazole) were synthesized. The series is completed by complex 4 with [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole as A and phenoxatellurine as D. Structures of complexes 2-4 were characterized by single-crystal X-ray diffraction (XRD), as well as solution and solid-state UV/Vis spectroscopy. Thermodynamics of their formation were obtained by density functional theory (DFT) calculations, their bonding situations were analyzed by quantum theory of atoms in molecules (QTAIM) calculations and dimer model energies of interactions quantified in the framework of the Hirshfeld surface (HS) analysis. With DFT calculations, the largest value of CT between D and A was found for complex 2, with 0.027 e in the XRD structure and 0.150 e in the optimized structure in MeCN. In the UV/Vis spectra, the λ of the CT bands of 2-4 varied in the range λ=517-705 nm. Model energy calculations for 1-4 revealed the importance of both dispersion interactions and hydrogen bonding between D and A as contributors to CT in the crystalline state. In an attempt to enlarge the CT value with bis[1,2,5-thiadiazolo][3,4-b;3',4'-e]pyrazine as A and 4-amino-2,1,3-benzoselenadiazole as D, an unprecedented 1:1 addition reaction was observed upon formation of a C-N bond between atom C7 of D and pyrazine atom N4 of A, accompanied by hydrogen atom transfer from C7 to another pyrazine atom N8 (compound 5). According to DFT calculations, the reaction is a multistep process featuring diradical intermediates and hydrogen atom intramolecular migration over four positions. Molecular and crystal structures of 5 (solvate with toluene) were elucidated by XRD and the crystal structure revealed a rather unusual porous framework.

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ChemInform Abstract: Reactions of 1,2‐Bis(trimethylsilyl)imines with Selenium and Tellurium Halogenides.

Neidlein¹,

Knecht²

1987

ChemInform

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Reaktionen von 1,2‐Bis(trimethylsilyl)iminen mit Selen‐und Tellur‐halogeniden

Abstract: Reactions of 1,2-Bis(trimethylsilyl)imines with Selenium and Tellurium HalogenidesThe reactions of benzil-bis(trimethylsi1yl)imine and phenanthrene-9,lO-bis(trimethylsilyl)imine with SeOCI,, SeCI4, and TeCI, are described. Alkali-bis(trimethylsily1)amide

Cited by 14 publications

References 12 publications

Product Class 27: Selenazoles and Tellurazoles Containing One or More Other Heteroatoms

Product Class 27: Selenazoles and Tellurazoles Containing One or More Other Heteroatoms

New Charge‐Transfer Complexes with 1,2,5‐Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction

ChemInform Abstract: Reactions of 1,2‐Bis(trimethylsilyl)imines with Selenium and Tellurium Halogenides.

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