42858-37-7

Basic information

• Product Name: Cyclododecanone, 2-(phenylseleno)-
• CAS NO: 42858-37-7
• Molecular Formula: C18H26OSe
• Molecular Weight: 337.364
• Mol File: 42858-37-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Cyclododecanone, 2-(phenylseleno)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclododecanone, 2-(phenylseleno)-(42858-37-7)
• EPA Substance Registry System: Cyclododecanone, 2-(phenylseleno)-(42858-37-7)

Safety Data

• Hazardous Substances Data: 42858-37-7(Hazardous Substances Data)

Upstream product

• 1666-13-3 diphenyl diselenide 
• 830-13-7 cyclododecanone 
• 5707-04-0 Phenylselenyl chloride 
• 55314-44-8 [((E)-Cyclododec-1-enyl)oxy]-trimethyl-silane 
• 1129-89-1 cis-cyclododecene 
• 68048-49-7 1-phenylseleno-2-decanone 
• 1501-82-2 cyclododecene 
• 72474-91-0 2-(phenylseleno)cyclododecan-1-ol 

Downstream Products

• 830-13-7 cyclododecanone 
• 104755-29-5 C₁₈H₂₆Cl₂OSe 

Relevant articles and documents

Halogen and chalcogen cation pools stabilized by DMSO. Versatile reagents for alkene difunctionalization

Halogen and chalcogen cations (X+ = Br+, I +, ArS+, and ArSe+) were generated by low-temperature electrochemical oxidation in the presence of dimethyl sulfoxide (DMSO) and were accumulated in the solution. DFT calculations indicated that DMSO stabilizes these cations by coordination. The complexes of I+ with one and two DMSO molecules were observed by cold-spray-ionization MS analyses. The stability of the resulting cation pools of X+ increased in the order of Br+ + + +, which could be explained in terms of the electronegativity of X. The cation pools served as versatile reagents for organic synthesis; the reactions with alkenes gave β-X-substituted alkoxysulfonium ions, which were converted to the corresponding carbonyl compounds by the treatment with triethylamine, whereas the treatment with methanol gave the corresponding alcohols. The reactions with aminoalkenes and 1,6-dienes gave the cyclized products.

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.

One -step Oxidation of Olefins into α-Phenylseleno Carbonyl Compounds

Oxidation of olefins has been examined with the following three types of reagents; (i) (C6H5Se)2-Br2-(Bu3Sn)2O, (ii) (C6H5Se)2-t-BuOOH, and (iii) (C6H5Se)2-(C6H5SeO)20, and the corresponding α-phenylseleno carbonyl compounds have been obtained directly from the olefins.