New Insights in Frustrated Lewis Pair Chemistry with Azides.

ABSTRACT: The geminal frustrated Lewis pair (FLP) tBu₂ PCH₂ BPh₂ (1) reacts with phenyl-, mesityl-, and tert-butyl azide affording, respectively, six, five, and four-membered rings as isolable products. DFT calculations revealed that the formation of all products proceeds via the six-membered ring structure, which is thermally stable with an N-phenyl group, but rearranges when sterically more encumbered Mes-N₃ and tBu-N₃ are used. The reaction of 1 with Me₃ Si-N₃ is believed to follow the same course, yet subsequent N₂ elimination occurs to afford a four-membered heterocycle (5), which can be considered as a formal FLP-trimethylsilylnitrene adduct. Compound 5 reacts with hydrochloric acid or tetramethylammonium f

SUBMITTER: Boom DHA 

PROVIDER: S-EPMC6851766 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature