Reactions of 2-(Organylseleno)propenenitriles with Dimethyl Ethynedicarboxylate

✍ Scribed by Döpp, Dietrich ;Sturm, Thomas

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 615 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970315

✦ Synopsis

Abstract

(2‐tert‐Butylseleno)propenenitrile (12a) has been prepared and treated with dimethyl ethynedicarboxylate (3) and methyl propiolate (18) to give the 2,3‐dihydroselenophenes 16 and 21, respectively. In contrast, 2‐(ethylseleno)‐, 2‐(methylseleno)‐ and 2‐(phenylseleno)propenenitrile (12b–d) tend to form polysubstituted butadienes 17b–d with 3 by net organoylseleno group transfer from 12b–d to C‐2 of 3 following attachment of C‐3 of 17 to C‐3 of 3. Five‐membered selenonium ylides are proposed as intermediates.