A Facile Synthesis of Seleno- and Telluroformamides

Segi, Masahito; Kojima, Akihiro; Nakajima, Tadashi; Suga, Sohei

doi:10.1055/s-1991-20643

Cited by 37 publications

(10 citation statements)

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“…Interestingly, the selenation of selenourea 2 by using WR led to the new selenoformamide 5 in 88% yield as a unique isolatable product, along with phosphorus-containing byproducts derived from WR. Although the sterically demanding selenoformamide 5 was never produced previously, its analogues have been prepared from the reaction of amides and Al-E [a mixture of ( i Bu 2 AlE) 2 and ( i Bu 2 AlE) n , E = S, Se and Te] reagents [ 21 , 22 ] or direct thionation and selenation of amides using elemental sulfur and selenium and hydrochlorosilanes in the presence of amines [ 23 ].…”

Section: Resultsmentioning

confidence: 99%

Diverse Derivatives of Selenoureas: A Synthetic and Single Crystal Structural Study

Hua

Cordes

et al. 2018

Molecules

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Reacting aroyl chlorides with an equivalent of potassium selenocyanate, followed by treating with an equivalent of 1,2,4-tri-tert-butylaniline at room temperature, resulted in the expected selenoureas and unusual diselenazoles. The selenation of selenourea by Woollins Reagent gave a new selenoformamide. Nucleophilic addition of selenoureas with acyl bromides led to the formation of new carbamimidoselenoates rather than the expected 1,3-selenazoles. The novel compounds prepared were characterised spectroscopically and crystallographically.

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Section: Resultsmentioning

confidence: 99%

Diverse Derivatives of Selenoureas: A Synthetic and Single Crystal Structural Study

Hua

Cordes

et al. 2018

Molecules

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“…Syntheses 4-(Telluroformyl)morpholine (1a) and 4-(selenoformyl)morpholine (1b) were prepared according to published procedures [18,25]. PyM(CO) 5 , where M is Cr, Mo, and W, were easily prepared by the reaction between the respective hexacarbonyls and pyridine in refluxing xylene.…”

Section: Resultsmentioning

confidence: 99%

“…Identification of PyCr(CO) 5 Preparation of 4-(Selenoformyl )morpholine C 5 H 9 NOSe (1b). The procedure reported by Segi and co-workers [25] was used. 4-(Selenoformyl)morpholine, C 5 H 9 NOSe (480 mg, 82.7%), was obtained in the form of a yellow solid (mp 77.0-78.0ЊC) from the reaction between 4-formylmorpholine (400 mg, 3.44 mmol) and Me 2 AlSeAlMe 2 .…”

Section: Preparation Of Metal Pyridine Pentacarbonylsmentioning

confidence: 99%

Telluroamides and selenoamides: Complexes with chromium, molybdenum, and tungsten pentacarbonyls

Reibenspies

Zingaro

1998

Heteroatom Chem.

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Several new telluroamide and selenoamide group 6 metal complexes (2a–2f), C5H9NOE‐M(CO)5, where E is Te or Se and M is Cr, Mo, or W, have been successfully synthesized by the reaction between PyM(CO)5 and 4‐(telluroformyl)morpholine (1a) or 4‐(selenoformyl)morpholine (1b). The crystal structures of C5H9NOSe (1b), C5H9NOTe‐Cr(CO)5 (2a), and C5H9NOSe‐Cr(CO)5 (2d) have been determined. The changes in the physical properties and structures between free ligands (1a, 1b) and coordinated telluro‐ or selenocarbonyls (in complexes 2a–2f) have been investigated. © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9:57–64, 1998

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“…The treatment of 4-methyl-, 4-methoxy-, 4chloro-, 4-nitro-and 4-cyanobenzoyl chlorides under reaction conditions similar to that for benzoyl chloride afforded the corresponding Se-aryl selenol esters in 71-91 % yields ( Table 2). In the coupling reaction of PhSeSnBu 3 (1) with aroyl or acyl chloride, the catalytic reaction pathways involving aroyl or acyl palladium intermediate (8), which is one of the active species, was proposed. Similarly, the coupling reaction of 1 with acyl chlorides having a linear alkyl chain or benzylic group was successfully occurred, and Se-aryl selenol esters were obtained in 85 and 92 % yield.…”

Section: -2 Synthesis Of Se-phenyl Selenol Esters [17 18]mentioning

confidence: 99%

Utilization of Phenyl Trialkylstannyl Selenide as a Promising Reagent for Introduction of the Phenylseleno Group

Nishiyama¹,

Sonoda²

2005

MROC

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New synthetic methods of organoselenium compounds by the use of phenyl tributylstannyl selenide (PhSeSnBu 3 ) (1), which is a stable selenium reagent in air and moisture, as a phenylselenated reagent have been developed. In the presence of palladium complex catalyst, the reaction of 1 with organohalogen compounds took place efficiently to give the corresponding organoselenium compounds in moderate to good yields. Furthermore, it was found that Lewis acid assisted the reaction of 1 with oxygen-containing compounds giving the corresponding organoselenium compounds.

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A Facile Synthesis of Seleno- and Telluroformamides

Cited by 37 publications

References 0 publications

Diverse Derivatives of Selenoureas: A Synthetic and Single Crystal Structural Study

Diverse Derivatives of Selenoureas: A Synthetic and Single Crystal Structural Study

Telluroamides and selenoamides: Complexes with chromium, molybdenum, and tungsten pentacarbonyls

Utilization of Phenyl Trialkylstannyl Selenide as a Promising Reagent for Introduction of the Phenylseleno Group

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