The Structure and Thermal Stability of 1,2-Dimethoxycarbonyl-3,3-dimethylcyclopropene

Sangdon Han, Tina Arrowood, Victor G. Young, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The X-ray crystal structure of 1,2-dimethoxycarbonyl-3,3-dimethylcyclopropene (1) is reported and the geometry is contrasted to that of cyclopropene (2) and 3,3-dimethylcyclopropene (3). Ab initio and density functional theory calculations were carried out in order to examine the conformational preference of the ester groups (i.e., s-cis vs. s-trans) and to probe the thermal stability of 1 via a model compound, 1-methoxycarbonyl-3-methylcyclopropene. Experimental activation parameters for the unimolecular isomerization were measured and compared to an analogous dibenzoylcyclopropene derivative.

Original languageEnglish (US)
Pages (from-to)349-354
Number of pages6
JournalStructural Chemistry
Volume10
Issue number5
DOIs
StatePublished - Jan 1 1999

Keywords

  • Cyclopropene derivatives
  • Molecular orbital calculations
  • Unimolecular isomerization
  • X-ray analysis

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