Ring Opening of Cyclopropanone

A. Liberles, A. Greenberg, A. Lesk

Research output: Contribution to journalArticle

46 Scopus citations

Abstract

We report the results of INDO and ab initio SCF calculations on cyclopropanone, oxyallyl, and aliene oxide, and the con- and disrotatory openings of the closed ketone. The ab initio results indicate that singlet oxyallyl is 83 kcal/mol less stable than cyclopropanone, while aliene oxide is 21 kcal/mol less stable. The internal C3C1C2 angle in singlet oxyallyl is predicted to be near 105°. Although the conrotatory opening of cyclopropanone passes through a true transition state, the disrotatory opening is the lower energy pathway, and oxyallyl appears to be at, or near, the disrotatory energy maximum.

Original languageEnglish (US)
Pages (from-to)8685-8688
Number of pages4
JournalJournal of the American Chemical Society
Volume94
Issue number25
DOIs
StatePublished - Dec 1 1972

All Science Journal Classification (ASJC) codes

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

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