58646-01-8

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 114050-31-6 3-Phenyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 122-78-1 phenylacetaldehyde 
• 910318-64-8 2-cyanoethyl 2-phenylethyl selenide 
• 4455-09-8 2-phenylethyl tosylate 
• 622-24-2 2-phenylethyl chloride 

Downstream Products

• 157030-93-8 ethyl 2-phenylethylselenoacetate 
• 157030-92-7 2-phenylethylselenoacetonitrile 
• 108775-78-6 2-phenylethaneselenolate 

Relevant academic research and scientific papers

An efficient and practical method for the selective synthesis of sodium diselenide and diorganyl diselenides through selenium reduction

Studies on an efficient and practical method for the selective synthesis of diorganyl diselenides over diorganyl selenides are presented. Considering the discrepancies between reports on organoselenium compounds, we wanted to establish a tolerable synthetic method for diorganyl diselenides and investigate their characteristics. We optimized reaction conditions for sodium diselenide preparation using selenium, NH2NH2·H2O, and NaOH and, by treating the obtained sodium diselenide with various alkyl or aryl halides, achieved the selective synthesis of diorganyl diselenides in modest to good yields (57–88%) with good reproducibility. We further studied the mechanistic implication, the effects of solvent changes, and the stability of diorganyl diselenides.

A rapid, efficient and green procedure for transformation of alkyl halides/ tosylates to organochalcogens in water

A one-pot and efficient synthesis of dialkyl dichalcogenides (S, Se) in aqueous media under catalyst-free conditions using benzylic, allylic and primary halides with elemental sulfur and selenium has been developed. Also, this procedure was extended to preparation of trisulfides and triselenides from secondary and tertiary halides in same condition. In all cases, products can be obtained in good to excellent yield in short reactions time.

Redox chemistry of selenenic acids and the insight it brings on transition state geometry in the reactions of peroxyl radicals

The redox chemistry of selenenic acids has been explored for the first time using a persistent selenenic acid, 9-triptyceneselenenic acid (RSeOH), and the results have been compared with those we recently obtained with its lighter chalcogen analogue, 9-tr

Transition-metal-free synthesis of unsymmetrical diaryl chalcogenides from arenes and diaryl dichalcogenides

A transition-metal-free synthetic method has been developed for the synthesis of unsymmetrical diaryl chalcogenides (S, Se, and Te) from diaryl dichalcogenides and arenes under oxidative conditions by using potassium persulfate at room temperature. Variously substituted arenes such as anisole, thioanisole, diphenyl ether, phenol, naphthol, di- and trimethoxy benzenes, xylene, mesitylene, N,N-dimethylaniline, bromine-substituted arenes, naphthalene, and diaryl dichalcogenides underwent carbon-chalcogen bond-forming reaction to give unsymmetrical diaryl chalcogenides in trifluoroacetic acid. To understand the mechanistic part of the reaction, a detailed in situ characterization of the intermediates has been carried out by 77Se NMR spectroscopy by using diphenyl diselenide as the substrate. 77Se NMR study suggests that electrophilic species ArE+ is generated by the reaction of diaryl dichalcogenide with persulfate in trifluoroacetic acid. The electrophilic attack of arylchalcogenium ion on the arene may be responsible for the formation of the aryl-chalcogen bond.

4-SE-THYMIDINE DERIVATIVES, 4-SE-URIDINE DERIVATIVES, DI (2-CYANOETHYL) DISELENIDE, AND METHODS

A compound having the formula (I): wherein R1 is H, HO, acyl-O, TOM-O, ACE-O, alkyl-O, orthoester, TBDMS-O, HSe, diselenide, or alkyl-Se, R2 is H, HO, acyl-O, TOM-O, ACE-O, CH3-Se, alkyl-O, TBDMS-O, TMS-O, HSe, diselenide, alkyl-Se, phosphoramidite, phosphoroselenoamidite, phosphate, phosphoroselenoate, a 5'linked nucleotide, a 5'linked seleno-nucleotide, a 5'linked oligonucleotide, a 5'linked seleno-oligonucleotide, a 5'linked nucleic acid chain, or a 5'linked seleno-nucleic acid chain, R3 is H, HO, acyl-O, alkyI-O)3Si-O, BzH-O, DOD-O, alkyl-O, TBDMS-O, HSe, diselenide, alkyl-Se, DMTr- O, phosphate, phosphoroselenoate, diphosphate, diphosphoroselenoate, triphosphate, triphosphoroselenoate, a 3'linked nucleotide, a 3'linked oligonucleotide, a 3'linked nucleotide, a 3'linked oligonucleotide, or a nucleic acid chain, R4 is H or CH3, and X is an oxygen atom or selenium atom.

A simple strategy for incorporation, protection, and deprotection of selenium functionality

Synthesis of di-2-cyanoethyl diselenide is reported for the first time. Using this reagent, incorporation and protection of selenium functionality can be achieved in one step with high yield, and the deprotection condition is mild, which allows alkylation simultaneously. Georg Thieme Verlag Stuttgart.

Efficient reductive selenation of aromatic aldehydes to symmetrical diselenides with Se/CO/H2O under atmospheric pressure

An efficient method for the synthesis of symmetrical diselenides is described. Reductive selenation of aromatic and heterocyclic aromatic aldehydes (ArCHO) with Se/CO/H2O in DMF afforded diselenides (ArCH 2SeSeCH2-Ar) in y

The invention of radical reactions. Part XXXVII. A convenient radical synthesis of dialkyl diselenides from carboxylic acids

A new and convenient synthesis of dialkyl diselenides from carboxylic acids by Barton PTOC ester based radical chemistry is described. This method was especially successful when O-cholestan-3β-yl-2,2,2-trichloroselenoacetate and O-neopentyl selenobenzoate

Generation of selenabenzenes bearing an electron-withdrawing group at the 2-position

3,6-Dihydro-2H-selenopyrans 2 with an electron-withdrawing group at the 2-position were prepared by the Diels-Alder reaction of butadienes with selenoaldehydes generated in situ from selenocyanates 1 and triethylamine. Oxidation of the dihydroselenopyraus 2 with 1.5 eq of m-chloroperbenzoic acid provided 2H-selenopyraus 9 and 3,6-dihydro-2H-selenopyran-2-yl m-chlorobenzoates 10. The benzoates 10 were smoothly converted into the selenopyrans 9 using polyphosphoric acid trimethylsilyl ester. The selenopyrans 9 were methylated with methyl trifluoromethanesuflonate to give Se-methyl selenopyranium trifluoromethanesulfonates 12. Deprotonation of the selenonium salts 12 with sodium hydride or triethylamine generated the selenabenzene derivatives 13, but they were too unstable to be isolated. Therefore, we confirmed the generation of 13 by 1H- and 13C-NMR spectroscopy at -30°C.

A New Method of Generation of α-Selenocarbenium Ions from Se,O-Heteroacetals and Their Reactions

Various Se,O-heteroacetals were prepared by the LiAlH4 reduction of diselenides 1 followed by alkylation with methoxymethyl chloride or (2-methoxyethoxy)methyl (MEM) chloride.Olefinic and acetylenic α-seleno carbenium ions were generated by the selective C-O bond cleavage of O-(2-methoxyethyl)-Se,O-heteroacetals with titanium(IV) chloride and cyclized to give the seleno heterocyclic compounds.Olefinic MEM-selenides 3a,b,d-f,h underwent the endo-mode cyclization to afford 4-chloroselenacycloalkanes 4a,b,d-f,h in good yields, whereas acetylenic MEM-selenides 12b-e,g-j underwent the exo-mode cyclization to give 3-(1-chloroalkylidene)selenacycloalkanes 13b-e,g-j.This new utilization of α-seleno carbenium ions was also applied to the intramolecular and intermolecular Friedel-Crafts reactions.