Solid base-catalyzed reaction of nitriles with methanol to form α,β-unsaturated nitriles I. Conversion and selectivity
✍ Scribed by Hideki Kurokawa; Tatsuro Kato; Wataru Ueda; Yutaka Morikawa; Yoshihiko Moro-oka; Tsuneo Ikawa
- Book ID
- 113179994
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- English
- Weight
- 583 KB
- Volume
- 126
- Category
- Article
- ISSN
- 0021-9517
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e-Acetoxy-8,y-unsaturated nitriles react at room temperature with malonates and acetoacetates in the presence of palladium-phosphine complexes as a catalyst to give y-substituted a,8-unsaturated nitriles selectively. Also yacetoxy-a,8-unsaturated ester was attacked at y-position by malonate.
## Abstract Diethyl (1‐cyanoethyl) phosphorate 1 was reacted with __n__‐butyl‐lithium in tetrahydrofuran (THF) at ‐ 78 °C and the resulting carbanion 2 reacted with perfluoroalkanoic add anhydride to afford perfluoroacylated phosphorate 3. Without isolation 3 was attacked by Grignard reagents givin