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Issue 39, 2017
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Photochemical generation and trapping of 3-oxacyclohexyne

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Abstract

The strained heterocyclic alkyne, 3-oxacyclohexyne, was generated photochemically for the first time using a cyclopropanated phenanthrene precursor, and trapped by cyclopentadienones as Diels–Alder adducts. The precursor initially produced the putative 3-oxacyclopentylidenecarbene that subsequently rearranged to the cycloalkyne. Computational studies indicate that the carbene favors a singlet state, and the barrier for its ring expansion by a 1,2-shift of the carbon proximal to oxygen is lower in energy than the corresponding shift of the distal carbon.

Graphical abstract: Photochemical generation and trapping of 3-oxacyclohexyne

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Supplementary files

Article information


Submitted
11 Jul 2017
Accepted
15 Sep 2017
First published
15 Sep 2017

Org. Biomol. Chem., 2017,15, 8270-8275
Article type
Communication

Photochemical generation and trapping of 3-oxacyclohexyne

R. Fan, Y. Wen and D. M. Thamattoor, Org. Biomol. Chem., 2017, 15, 8270
DOI: 10.1039/C7OB01697B

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