2011•European Journal of Organic ChemistryRequires access

Steric Course of the Electrophilic Substitution of a Lithiocarbanion Generated from (S,E)‐1‐Phenylbut‐2‐en‐1‐yl Diisopropylcarbamate and Solvent Effects

Hidaka Ikemoto, Michiko Sasaki, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda

Abstract

Abstract The effects of electrophiles and solvents on the stereochemistry of electrophilic substitution of a lithiocarbanion generated from (S,E)‐1‐phenylbut‐2‐en‐1‐yl diisopropylcarbamate were examined using various acids and carbon electrophiles. The stereochemical outcomes were influenced by the relative ability of the electrophiles and solvents to coordinate to lithium.

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Available abstract

Key concepts: Electrophile, Chemistry, Steric effects, Electrophilic substitution, Substitution reaction, Lithium (medication), Stereochemistry, Solvent