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 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
Volume101
Issue number5
Publication statusPublished - 1979 Dec 1
Externally publishedYes

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Dimethyl sulfoxide
Iodides
Negative ions
Alkenes
Dimethyl Sulfoxide
Anions
methyl tosylate

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Orientation in base-promoted 1,2-elimination reactions. Influence of β-alkyl and leaving groups upon the threshold for base steric effects. / Bartsch, Richard A.; Read, Rita A.; Larsen, David T.; Roberts, Debra K.; Scott, K. Jane; Cho, Bong-Rae.

In: Journal of the American Chemical Society, Vol. 101, No. 5, 01.12.1979, p. 1176-1181.

Research output: Contribution to journalArticle

Bartsch, Richard A. ; Read, Rita A. ; Larsen, David T. ; Roberts, Debra K. ; Scott, K. Jane ; Cho, Bong-Rae. / Orientation in base-promoted 1,2-elimination reactions. Influence of β-alkyl and leaving groups upon the threshold for base steric effects. In: Journal of the American Chemical Society. 1979 ; Vol. 101, No. 5. pp. 1176-1181.
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