Methyl phenylacetate enolate generated with the P4-tBu Schwesinger base: ‘naked’ or not?

✍ Scribed by Jean-Sébastien Fruchart; Hélène Gras-Masse; Oleg Melnyk

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 127 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01994-3

✦ Synopsis

NMR studies revealed that methyl phenylacetate enolate generated with the P4-tBu phosphazene base was 'naked' or tightly associated with P4-tBuH + cation depending on very small variations in solvent composition. Both forms reacted more rapidly than the corresponding lithium enolate in a model alkylation experiment using dimethyl sulfate.