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. Author manuscript; available in PMC: 2024 Sep 29.
Published in final edited form as: Science. 2023 Sep 28;381(6665):1474–1479. doi: 10.1126/science.adj5331

Fig. 2. Design and mechanism.

Fig. 2.

(A) Design hypothesis for ipso-carbon deletion of azepines. (B) Precedent in benzenoid systems, demonstrating hybridization effects. (C) Discovery of oxidant-dependent cyclization and thermolytic extrusion of pyridine, with optimized conditions and control experiments lacking a pendant alcohol. (D) Computed mechanism for carbene extrusion from spirocyclic azahexatriene. NBS, N-bromosuccinimide; NBC, N-bromocaprolactam; decomp., decomposition; conv., conversion; DBU, diazabicycloundecene; OTBS, tert-butyldimethylsilyloxy.