Internal B-O Bond-Facilitated Photoisomerization of Boranes: Ring Expansion Versus Oxyborane Elimination/Intramolecular Diels-Alder Addition

Guo Fei Hu, Hai Jun Li, Chao Zeng, Xiang Wang, Nan Wang, Tai Peng, Suning Wang*

*Corresponding author for this work

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Abstract

Boron compounds (1-4) containing an internal B-O bond have been found to undergo facile multistructural transformations upon irradiation at 365 or 410 nm, generating rare 8-membered B,O-heterocycles (1c-4c). In addition, 2 and 3 also undergo an intramolecular Diels-Alder addition and oxyborane elimination concomitantly, via intermediates 2b/3b, producing 2d/3d. The pathways to isomer c and product d were found to be a thermal process and a photo process, respectively.

Original languageEnglish
Pages (from-to)5285-5289
Number of pages5
JournalOrganic Letters
Volume21
Issue number13
DOIs
Publication statusPublished - 20 Jun 2019

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Hu, G. F., Li, H. J., Zeng, C., Wang, X., Wang, N., Peng, T., & Wang, S. (2019). Internal B-O Bond-Facilitated Photoisomerization of Boranes: Ring Expansion Versus Oxyborane Elimination/Intramolecular Diels-Alder Addition. Organic Letters, 21(13), 5285-5289. https://doi.org/10.1021/acs.orglett.9b01892