77461-49-5

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 35167-28-3 vinyl phenyl selenide 
• 13683-41-5 1-bromo-1-(trimethylsilyl)ethene 
• 34837-55-3 Phenylselenyl bromide 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 135631-15-1 (4E)-1-Phenylseleno-1-trimethylsilylhexa-1,4-dien-3-one 
• 143397-01-7 r-1-(phenylseleno)-c-2-propionyl-1-(trimethylsilyl)cyclobutane 
• 135631-26-4 Phenyl cyclopent-1-ene-1-carboselenoate 
• 135631-19-5 4-(Phenylseleno)bicyclo<3.3.0>oct-3-en-2-one 
• 135631-13-9 1-(Cyclopent-1'-enyl)-3-(phenylseleno)-3-(trimethylsilyl)prop-2-en-1-one 
• 143370-47-2 c-1-benzoyl-r-2-(phenylseleno)-2-(trimethylsilyl)cyclobutane 
• 135631-21-9 4-Methyl-3-(phenylseleno)cyclopent-2-enone 
• 135631-18-4 4-Methyl-5-(phenylseleno)-3-(trimethylsilyl)cyclopent-2-enone 
• 135631-20-8 9-(Phenylseleno)bicyclo<4.3.0>non-8-en-7-one 
• 135631-17-3 1-(Phenylseleno)-4-(trimethylsilyl)bicyclo<3.3.0>oct-3-en-2-one 
• 135631-24-2 3,5-Bis(phenylseleno)-4-methylcyclopent-2-enone 
• 135650-63-4 6-(Phenylseleno)-9-(trimethylsilyl)bicyclo<4.3.0>non-8-en-7-one 
• 135631-14-0 1-(Cyclohex-1'-enyl)-3-(phenylseleno)-3-(trimethylsilyl)prop-2-en-1-one 
• 143370-53-0 c-1-acetyl-r-2-(phenylseleno)-2-(trimethylsilyl)cyclobutane 

Relevant academic research and scientific papers

A Novel Competition between C-Se and C-Si Cleavage in Cyclization of β-Seleno-β-silyl-substituted Divinyl Ketones

Reactions of β-seleno-β-silyl-substituted divinyl ketones 2-4 with Lewis acid at room temp. gave phenylseleno and/or trimethylsilyl functionalized cyclopentanones.The use of TiCl4 or SnCl4 results in C-Se cleavage leading to 5-(phenylseleno)-3-(trimethylsilyl)cyclopent-2-enones 9-11 as major products.In contrast, using AgBF4-TMSCl (trimethylsilyl chloride) results in C-Si cleavage to give 3-(phenylseleno)cyclopenten-2-ones 12-14.Lewis acid-dependent competitive cleavage between C-Se and C-Si bonds has been demonstrated.

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.