57205-03-5

Upstream product

• 1666-13-3 diphenyl diselenide 
• 22081-48-7 (cyclohept-1-en-1-yloxy)(trimethyl)silane 
• 502-42-1 cycloheptanone 
• 71098-88-9 N-phenylselanylphthalimide 
• 60466-52-6 (Phenylseleno)methyltriphenylphosphonium bromide 
• 5707-04-0 Phenylselenyl chloride 

Downstream Products

• 1121-66-0 2-Cyclohepten-1-one 
• 104755-27-3 C₁₃H₁₆Cl₂OSe 
• 85283-17-6 N-[3-tert-Butyl-cyclohept-(E)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine 
• 85283-18-7 N-[3-tert-Butyl-cyclohept-(Z)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine 
• 344876-40-0 C₁₇H₂₅BrN₂O₂S 
• 344876-41-1 C₁₇H₂₅ClN₂O₂S 

Relevant academic research and scientific papers

K2S2O8-promoted C-Se bond formation to construct α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds

A novel K2S2O8-promoted C-Se bond formation from cross-coupling under neutral conditions has been developed. A variety of aldehydes and ketones react well using K2S2O8 as the oxidant in the absence of catalyst and afford desired products in moderate to excellent yields. This protocol provides a very simple route for the synthesis of α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds.

N, N, N -Triphenylselenylisocyanuric Acid (TPSCA): A New Versatile Reagent for α-Phenylselenenylation of Aldehydes and Ketones

A new, versatile reagent, N,N,N-triphenylselenyl-isocyanuric acid (TPSCA) has been prepared, characterized, and used as a source of the electrophilic phenylselenyl group. This relatively stable compound was utilized for an efficient α-selenenylation react

α-Phenylselenenylation of aldehydes and ketones with diphenyl diselenide mediated by KF/Al2O3

The utility of KF/Al2O3 for the synthesis of α-phenylseleno aldehydes and ketones from the corresponding aldehydes or ketones and diphenyl diselenide has been investigated. Simple stirring of a mixture of aldehyde or ketone and diphe

ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS

The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo--selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R", NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R" are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R" form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R" are attached; and wherein said compound is free from a metal catalyst.

Direct, facile aldehyde and ketone α-selenenylation reactions promoted by L-prolinamide and pyrrolidine sulfonamide organocatalysts

A new catalytic method for direct α-selenenylation reactions of aldehydes and ketones has been developed. The results of exploratory studies have demonstrated that L-prolinamide is an effective catalyst for α-selenenylation reactions of aldehydes, whereas

New Mild Methodology for the Synthesis of α-Phenylthio and α-Phenylseleno Ketones

Treatment of trimethylsilyl enol ethers with the adduct 1, derived from chloramine-T and (PhS)2, gave good yields of α-phenylthioketones.The selenium version of this reagent 2 gave α-phenylselenoketones.

Methods for the introduction of a Phenylselenium Dichloride Group into he α-position of Carbonyl Compounds. Syntheses of Enones.

Phenylselenium trichloride, PhSeCl3, direcly introduced, in fair yield, a PhSeCl2 group into the α-position of ketones with loss of HCl.To some extent, depending on the substrate, this reagent was also shown to act as a chlorinating agent toward ketones, yielding α-chloro ketones and α-phenylselenenyl ketones.The latter compounds were readily converted to selenium(IV) dichlorides by SO2Cl2 chlorination to significantly improve the overall yields of the selenetion process.The consecutive treatment of ketones with PhSeCl and SO2Cl2 could also be used for the introduction of a PhSeCl2 group, but this procedure was usually less efficient than the PhSeCl3-based one.Unsymmetrical ketones were selenated with poor regiocontrol.Aldehydes were primarily chlorinated by treatment with PhSeCl3, but consecutive treatment with PhSeCl3 and SO2Cl2 introduced a PhSeCl2 group into the α-position.Carboxylic acids and esters were ureactive toward PhSeCl3 and PhSeCl.PhSeCl3 underwent addition reactions with enones to introduce a PhSeCl2 group α or β to the carbonyl group, depending on the substrate.The carbonyl compounds substituted in the α-position with a PhSeCl2 group were easily converted to the corresponding α,β-unsaturated carbonyl compounds after hydrolysis/selenoxide elimination.Since the selenium(IV) intermediates involved were highly crustalline and easy to purify, the preparation of enones from symmetrical ketones via PhSeCl2 introduction/hydrolytic elimination was especially convenient to perform from the operational point of view.

Perhydroazulenes. 4. The 6-tert-Butyl-4-oxoperhydroazulene System

The four diastereoisomeric 6-tert-butyl-4-oxoperhydroazulenes (3-6) have been prepared and characterized.Molecular mechanics calculations suggest that each of these ketones will exist as one or both of a pair of closely related conformers as follows: 3, C-3 or TC-7; 4, TC-1 or TC-2; 5, B-3 or TB-4; 6, TC-4 or TC-5.A combination of 1H NMR data and X-ray crystallographic data support the correctness of these predictions.

A CONVENIENT METHOD FOR THE SYNTHESIS OF α-PHENYLSELENENYL CARBONYL COMPOUNDS

Treatment of ketones or aldehydes with selenium dioxide and diphenyl diselenide in the presence of acid catalyst afforded the corresponding α-phenylselenenyl carbonyl compounds in good yields.

A FACILE ACCESS TO α-PHENYLSELENENYL CARBONYL COMPOUNDS BY ELECTROCHEMICAL OXIDATION

A novel α-phenylselenenylation of carbonyl compounds has been performed by electrolysis of a solution of ketones, diphenyl diselenide, tetraethyl-ammonium bromide, and magnesium bromide in polar solvents (MeOH, AcOH, MeCN).The electrolysis enables us to p