Issue 39, 2017

Photochemical generation and trapping of 3-oxacyclohexyne

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

Supplementary files

Article information

Article type
Communication
Submitted
11 ก.ค. 2560
Accepted
15 ก.ย. 2560
First published
15 ก.ย. 2560

Org. Biomol. Chem., 2017,15, 8270-8275

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements