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

doi:10.1021/acs.orglett.9b01892

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

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

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 language	English
Pages (from-to)	5285-5289
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.9b01892
Publication status	Published - 20 Jun 2019

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

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.",

author = "Hu, {Guo Fei} and Li, {Hai Jun} and Chao Zeng and Xiang Wang and Nan Wang and Tai Peng and Suning Wang",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b01892",

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T1 - Internal B-O Bond-Facilitated Photoisomerization of Boranes

T2 - Ring Expansion Versus Oxyborane Elimination/Intramolecular Diels-Alder Addition

AU - Hu, Guo Fei

AU - Li, Hai Jun

AU - Zeng, Chao

AU - Wang, Xiang

AU - Wang, Nan

AU - Peng, Tai

AU - Wang, Suning

PY - 2019/6/20

Y1 - 2019/6/20

N2 - 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.

AB - 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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U2 - 10.1021/acs.orglett.9b01892

DO - 10.1021/acs.orglett.9b01892

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SN - 1523-7060

VL - 21

SP - 5285

EP - 5289

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

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

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