Orientation in Base-Promoted 1, 2-Elimination Reactions. Influence of β-Alkyl and Leaving Groups upon the Threshold for Base Steric Effects

Richard A. Bartsch, Rita A. Read, David T. Larsen, Debra K. Roberts, K. Jane Scott, Bong Rae Cho

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1176-1181
Number of pages6
JournalJournal of the American Chemical Society
Volume101
Issue number5
DOIs
Publication statusPublished - 1979 Feb 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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