Orientation is reported for eliminations from 2-butyl iodide and tosylate, 4-methyl-2-pentyl iodide and tosylate, and 4, 4-dimethyl-2-pentyl tosylate promoted by oxy anion bases in dimethyl sulfoxide. The level of base complexity which is necessary for the onset of base steric effects is influenced by the 0-alkyl group, but not the leaving group. A syn elimination pathway is apparent for the formation of trans-4, 4-dimethyl-2-pentene from 4, 4-dimethyl-2-pentyl tosylate.
ASJC Scopus subject areas
- Colloid and Surface Chemistry