1,4,7-trimethyloxatriquinane: SN2 reaction at tertiary carbon

Mark Mascal, Nema Hafezi, Michael D. Toney

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The synthesis of 1,4,7-trimethyloxatriquinane (1), a 3-fold tertiary alkyl oxonium salt, is described. Compound 1 is inert to solvolysis with alcohols, even at elevated temperatures, but undergoes facile substitution with the strongly nucleophilic azide anion. Since an SN1 pathway is excluded, the only reasonable mechanistic interpretation for the reaction between 1 and N3 - is SN2, despite the fact that substitution is occurring at a tertiary carbon center. This finding is supported by computational modeling and a study of the reaction kinetics, and is also consistent with observed solvent and salt effects.

Original languageEnglish (US)
Pages (from-to)10662-10664
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number31
DOIs
StatePublished - Aug 11 2010

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Substitution reactions
Carbon
Salts
Azides
Reaction kinetics
Anions
Alcohols
Negative ions
Temperature
1,4,7-trimethyloxatriquinane
hydronium ion

ASJC Scopus subject areas

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

Cite this

1,4,7-trimethyloxatriquinane : SN2 reaction at tertiary carbon. / Mascal, Mark; Hafezi, Nema; Toney, Michael D.

In: Journal of the American Chemical Society, Vol. 132, No. 31, 11.08.2010, p. 10662-10664.

Research output: Contribution to journalArticle

Mascal, Mark ; Hafezi, Nema ; Toney, Michael D. / 1,4,7-trimethyloxatriquinane : SN2 reaction at tertiary carbon. In: Journal of the American Chemical Society. 2010 ; Vol. 132, No. 31. pp. 10662-10664.
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