The 1,3 sigmatropic rearrangements of methyltriazene exhibit interesting behavior compared to their carbon analog (1-butene) in that electronic structure calculations indicate that methyltriazene favors an antarafacial with retention pathway for methyl shifts while 1-butene favors a suprafacial with inversion pathway. The origin of this phenomenon has been explored by comparing the transition states for the series of analogous compounds with varying numbers and locations of nitrogen and carbon atoms in the “backbone”, i.e., butene, propanimine, diazene, methylidene amine, methanimidamide, and triazene.<br/>

1,3-sigmatropic rearrangements in triazene and its carbon analogs

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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