55163-72-9

Upstream product

• 67-56-1 methanol 
• 108415-93-6 1-ethoxy-1-phenyl-2-phenylselenylethane 
• 64-17-5 ethanol 
• 63603-28-1 1-methoxy-1-phenyl-2-phenylselenoethane 
• 55221-03-9 (R)-2-methoxy-2-phenylethyl 4-methylbenzenesulfonate 
• 101-48-4 phenylacetaldehyde dimethyl acetal 

Relevant academic research and scientific papers

Synthesis of chiral acetals by asymmetric selenenylations

Asymmetric selenenylations of (E)-ethoxystyrene are described leading to chiral acetals. An efficient synthesis of such compounds including the determination of their absolute configuration is described.

ELABORATION OF THE ACYL LIGAND IN (η5-C5H5)Fe(CO)(PPh3)(COCH2OCH3)

Deprotonation of the complex (η5C5H5)Fe(CO)(PPh3)(COCH2OCH3) leads to anion 7 which can be alkylated stereoselectively to products of RFeRα/SFeSα configuration.Reaction of 7 with acetaldehyde or benzaldehyde are not stereoselective and yield four stereoisomeric products 16-19 or 20-23, respectively.Exchange of the lithium cation for diethylaluminium or divalent tin cations improves the stereoselectivity in reaction of 7 with carbonyl compounds.Reaction of 7 with acetone leads to product 24 of the RFeSα/SFeRα configuration.Decomplexation of 20with NBS and methanol is connected with decarbonylation and leads to mandelaldehyde dimethyl acetal.With other alcohols mixtures of diastereoisomeric mixed acetals are formed.Similar results are achieved with other mild oxidizing reagents as cerium ammonium nitrate or selenium dioxide.Oxidation of 20 with m-chloroperoxybenzoic acid leads mainly to one of the diastereoisomeric acetals although in a low yield.Decomplexation of 15 with NBS and ethanol leads to mixed acetal 29.

CONVERSION OF ALKYL PHENYL SELENIDES AND SELENOXIDES INTO DIALKYL ETHERS. NUCLEOFUGACITY ENHANCEMENT OF THE PLENYLSELENINYL GROUP BY meta-CHLOROPERBENZOIC ACID IN ALCOHOLS

The recently reported conversion of alkyl phenyl selenides into dialkyl ethers, promoted by MCPBA in alcohols, has been reinvestigated.It is concluded that the reactive intermediate does not derive from the selenones, as reported, but from the selenoxides.It is suggested that MCPBA adds to the selenoxide function to give an intermediate which easily gives rise to solvolysis; thus, the addition of MCPBA greatly enhances the nucleofugacity of the phenylseleninyl group.The synthesis and the reactivity of several 1-phenyl, 2-phenylseleninyl- and 1-phenyl-, 2-phenylselenonyl-ethanes are also described.