N,N-diethylbenzeneselenamide: a useful reagent for the direct selenenylation of aldehydes

✍ Scribed by Martin Jefson; Jerrold Meinwald

• Book ID: 104234290
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 199 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81958-4

✦ Synopsis

N,N-Diethylbenzeneselenamide reacts selectively with aldehydes, under mild conditions, to give a-phenylselenoaldehydes. N,N-Diethylbenzeneselenamide 1 reacts smoothly with 8-dicarbonyl compounds to give a-phenylseleno derivatives. 1 Whiz attempting to use this reaction to convert the malonic o-0 SeN (C,H,),

ester&into its a-phenylseleno derivative, 2, we were surprised to find that after 15 hours at room temperature in CH2C12, the major reaction product was the a-phenylselenoaldehydeA (Scheme 1). At short reaction times (~30 min), we isolated a mixture ofLand 4. Since dimethyl malonate itself could be selenenylated (60% yield) under similar condition, we suspected that the initial reaction product was in fact& and that this product rearranged to &under the reaction conditions. In support of this hypothesis, a mixture of&and&was transformed predominantly into Aupon treatzent with diethylanine in CH2C12 at R.T.