71996-27-5

Upstream product

• 67-56-1 methanol 
• 5707-04-0 Phenylselenyl chloride 
• 14088-61-0 2-diazocyclopentanone 
• 930-30-3 cyclopent-2-enone 
• 1666-13-3 diphenyl diselenide 
• 68845-73-8 tert-butyl(cyclopent-2-en-1-yloxy)dimethylsilane 
• 75608-73-0 α-chloro-α-phenylselenocyclopentanone 

Downstream Products

• 140110-71-0 cis-3-(Trimethylsilyl)-2-(phenylseleno)-2-(2-propenyl)-1-cyclopentanone 
• 140110-72-1 trans-3-(Trimethylsilyl)-2-(phenylseleno)-2-(2-propenyl)-1-cyclopentanone 
• 73824-93-8 cis-3-Methyl-2-(phenylseleno)cyclopentanone 
• 78763-74-3 3-Methyl-2-(phenylselenenyl)cyclopentanone 
• 119987-23-4 3-ethenyl-2-(phenylseleno)cyclopentanone 
• 10481-34-2 2-bromo-2-cyclopenten-1-one 
• 130490-22-1 2,3-dichloro-2-phenylselenenylcyclopentanone 
• 22354-39-8 2-benzyl-2-cyclopentenone 
• 118575-61-4 3-ethenyl-2-cyclopentenyl 2-diazo-4-phenyl-3-butenoate 
• 118575-68-1 (4α,8aα,8bα)-(+/-)-4,5,7,8,8a,8b-hexahydro-4-phenyl-2H-azuleno<1,8-bc>furan-2-one 
• 118575-52-3 3-ethenyl-2-cyclopentenyl 4-phenyl-3-butenoate 
• 1121-05-7 2,3-dimethylcyclopent-2-enone 
• 2758-18-1 3-Methyl-2-cyclopenten-1-one 

Relevant academic research and scientific papers

Formation of 2-phenylselenenylenones and 2-haloenones from enones. Mechanistic and synthetic aspects, X-ray crystal structures of intermediates

The structure of trans-3-chloro-2-phenylselenenylcyclohexanone (1) was determined by X-ray diffraction.Although this and similar compounds were readily dehydrohalogenated to give vinylic selenides, they were ruled out as intermediates in the synthesis of

Reactions of α-Diazo Ketones with Selenium-based Reagents. A General Synthesis of α-Chloro-, α-Bromo, α-Phenylseleno-, α-Acetoxy-, and α-Methoxy-αβ-unsaturated Ketones

Benzeneselenenyl derivatives, PhSe-X (X=Cl, Br, OCOCH3, and SCN) react readily with α-diazo ketones, RCOC(N2)R1 (R1=H or alkyl), with loss of nitrogen, furnishing αα-adducts of the type RCOCR1(X)SePh.The α-chloro and α-bromo adducts can be converted into α-methoxy adducts in methanol-sodium hydrogen carbonate.The utility of these adducts in synthesis is illustrated by their conversion (where structural considerations permit) via selenoxide fragmentation into α-heterosubstituted αβ-unsaturated ketones.Treatment of the series RCOCR1(X)SePh (R1=alkyl; X=Cl, Br, OCOCH3, and OCH3) with hydrogen peroxide-pyridine produces α-chloro-, α-bromo-, α-acetoxy-, and α-methoxy-αβ-unsaturated ketones, whereas treatment of series RCOCR1(X)SePh (R1=alkyl; X=Cl and Br) with lithium carbonate in dimethylformamide produces α-phenylseleno-αβ-unsaturated ketones.Several α-substituted cyclopentenones, cyclohexenones, and cycloheptenones have been synthesised in this way and acyclic examples are illustrated by the synthesis of 3-chloro-, 3-bromo-, 3-acetoxy-, 3-methoxy,-and 3-phenylselenobut-3-en-2-one from 3-diazobutan-2-one.

SYNTHETIC APPLICATIONS OF 2-PHENYLSELENENYLENONES-III AN OVERVIEW

2-Phenylselenenylenones are versatile species which can be selectively converted a number of different ketones and enones in high overall yields.

Oxidation of Olefins into α-Phenylseleno Carbonyl Compounds. Highly Regioselective anti-Markownikoff Type Oxidation of Allylic Alcohol Derivatives

By using (C6H5Se)2-t-BuOOH or (C6H5Se)(2-) (C6H5SeO)2O system, oxoselenylation reaction of C=C bonds have been examined with allylic and homoallylic alcohol derivatives, and substituted cyclohexenes, and allyl t-butyldimethylsilyl ethers are found to unde

Reactions of α-Diazoketones with Phenylselenenyl Chloride. A new Synthesis of α-Chloro- and α-Phenylselenenyl-α,β-unsaturated Ketones

α-Diazoketones react with phenylselenenyl chloride at room temperature giving α-chloro-α-phenylselenenyl ketones; where structural considerations permit these adducts can be transformed via elimination reactions into α-chloro- or α-phenylselenenyl-α,β-uns