66030-49-7

Upstream product

• 26822-85-5 1,1-bis(phenylseleno)ethane 
• 1666-13-3 diphenyl diselenide 
• 35167-28-3 vinyl phenyl selenide 
• 34837-55-3 Phenylselenyl bromide 

Downstream Products

• 74866-72-1 3-Methyl-5-phenyl-2-phenylselanyl-pent-1-en-3-ol 
• 74866-73-2 C₁₇H₁₈Se 
• 115476-64-7 3,3-Dichloro-5-phenylselanyl-dihydro-furan-2-one 
• 63017-57-2 isopropenyl phenylselenide 
• 35167-28-3 vinyl phenyl selenide 
• 1666-13-3 diphenyl diselenide 

Relevant academic research and scientific papers

Synthesis of selenoxides by oxidation of selenides with superoxide radical anions and 2-nitrobenzenesulfonyl chloride

Alkyl phenyl selenoxides were produced in excellent yields by oxidation of the corresponding selenides with 2-nitrobenzenesulfonyl chloride and potassium superoxide in dry acetonitrile at -15°C.

Bisannelation with vinylselenoxide: Synthesis of tricyclo[3.2.1.0(2,7)]octane-6-one and its Congeners

Reaction of kinetic enolate of α'-substituted cyclohexenone derivatives with vinylselenoxides provided tricyclo[3.2.1.0(2,7)]octane-6-one derivatives via domino Michael-Michael-substitution protocol. (C) 2000 Elsevier Science Ltd.

REACTIONS OF VINYL SELENOXIDES AND KETENES VIA 3,3-SIGMATROPIC REARRANGEMENT

The reactions of several vinyl selenoxides with chlorocyanoketene proceed via a 3,3-sigmatropic rearrangement of an enolate oxyselenonium species to yield seleno-substituted γ-butyrolactones.

Vinyl Selenides and Selenoxides: Preparation, Conversion to Lithium Reagents, Diels-Alder Reactivity, and Some Comparisons with Sulfur Analogues

A variety of aryl vinyl selenides are prepared by reaction of vinyl Grignard reagents with aryl selenyl bromides or by reductive elimination of the adducts of lithiums with carbonyl compounds.Deprotonation of phenyl vinyl selenide is achieved with LDA at -78 deg C in THF.Vinyl selenides with β-alkyl groups require LiTMP and warmer temperatures (-50 deg C) for complete deprotonation.Allylic lithium reagents were obtained from 1-propenyl and 2-methyl-1-propenyl selenides whereas 1-butenyl or 3-methyl-1-butenyl selenides gave vinyl lithium reagents.Reaction with electrophiles proceeds in good to excellent yield.Primary halides require HMPA to react well.Unhindered carbonyl compounds react without enolization.Deprotonation with LDA is shown to be reversible, and during competitive deprotonation studies with LDA, aryl vinyl sulfides are found to be thermodynamically less acidic than aryl vinyl selenides (KS/Se=0.21 for phenyl vinyl and 0.3 for m-(trifluoromethyl)phenyl vinyl).Deprotonation with LiTMP is shown to be irreversible, and competitive deprotonation studies showed vinyl selenide to be kinetically more acidic as well S/Se=0.37 (phenyl vinyl),0.42 (m-(trifluoromethyl)phenyl vinyl)>.Most studies have shown sulfur compounds to be more acidic. m-(Trifluoromethyl)phenyl allyl sulfide as expected, is more acidic than selenium compound (kS/Se=3.8).Vinyl selenoxides can be prepared with m-chloroperbenzoic acid.They are not thermally stable enough to serve as acetylene equivalents in Diels-Alder reactions.Phenyl vinyl selenide gives a Diels-Alder addition product with 1,4-diphenylisobenzofuran but failed to give cycloaddition products with less reactive dienes.Phenyl vinyl selenoxide does not give a useful yield of lithium reagent upon reaction with amide bases.