Computational and 13C investigations of the diazadienes and oxazadienes formed via the rearrangement of methylenecyclopropyl hydrazones and oximes

Bo Chen, Mark E. Scott, Bruce A. Adams, David A. Hrovat, Weston Thatcher Borden, Mark Lautens

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12 Scopus citations

Abstract

Computational and further experimental investigations of the previously reported diazadienes, obtained via the rearrangement of methylenecyclopropyl hydrazone 1 are reported. Calculations at the CCSD(T)/cc-pVTZ//B3LYP/6-31G(d) level of theory indicate that the initially reported product 3 would, if formed, undergo rapid electrocyclic ring opening and, hence, would be unstable under the reaction conditions. Based on this computational prediction, further analysis of the 13C NMR spectrum, previously attributed to 3, led to the revision of structure 3 to that of its N-tosylaminopyrrole constitutional isomer 11. Similarly, structure 8, formed in the rearrangement of oxime 6, was revised to that of N-hydroxypyrrole 12.

Original languageEnglish (US)
Pages (from-to)3930-3933
Number of pages4
JournalOrganic Letters
Volume16
Issue number15
DOIs
StatePublished - Aug 1 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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