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

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 elimi...

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Published inOrganic letters Vol. 21; no. 13; pp. 5285 - 5289
Main Authors Hu, Guo-Fei, Li, Hai-Jun, Zeng, Chao, Wang, Xiang, Wang, Nan, Peng, Tai, Wang, Suning
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.07.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
ISOMERIZATION
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01892