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

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13 Citations (Scopus)


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 β-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
Issue number5
Publication statusPublished - 1979 Dec 1
Externally publishedYes


ASJC Scopus subject areas

  • Chemistry(all)

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