The Mechanism of Oxygen Transfer from an Oxaziridine to a Sulfide and a Sulfoxide: A Theoretical Study

Robert D. Bach*, Barry A. Coddens, Joseph J.W. McDouall, H. Bernhard Schlegel, Franklin A. Davis

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

Abstract

Chiral oxaziridines provide synthetically useful reagents for the asymmetric transfer of an oxygen atom to a variety of substrates. One of the fundamental questions pertaining to the approach of the reactants is whether either of the lone pairs on the electrophilic oxygen exerts a significant electronic influence on the transition structure. Employing a model reaction system, we have found that oxygen atom transfer from an oxaziridine to a sulfoxide is essentially invarient to the torsional orientation of the two fragments in the transition state. The planar and spiro transition structures differ in energy by only 0.4 kcal/mol at the MP4SDTQ/4-31G(d) level of calculation. These data are consistent with experimental observations and with the earlier ab initio calculations on this type of oxygen atom transfer.

Original languageEnglish (US)
Pages (from-to)3325-3330
Number of pages6
JournalJournal of Organic Chemistry
Volume55
Issue number10
DOIs
StatePublished - Jan 1 1990

ASJC Scopus subject areas

  • Organic Chemistry

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