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Reactions of 2‐(Organylseleno)propenenitriles with Dimethyl Ethynedicarboxylate
Author(s) -
Döpp Dietrich,
Sturm Thomas
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970315
Subject(s) - chemistry , medicinal chemistry , stereochemistry
( 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.