Journal article

Publication year: 2014

Pages: 2410-2413

Journal: Organic Letters

Volume number: 16

Issue number: 9

ISSN: 1523-7060

Open access status: Bronze

DOI Link: https://doi.org/10.1021/ol5007604

Publisher: American Chemical Society

Abstract: 
While investigating the [2 + 2 + 2] cycloaddition as a tool to build up strained oligophenyl systems with a diyne-ethylene glycol macrocyle, a surprising change of mechanism was observed. Instead of the expected [2 + 2 + 2] para-terphenyl, the ortho-terphenyl product explained by a formal [2 + 1 + 2 + 1] cycloaddition was formed. An eta(4)-coordinated metal-cyclobutadiene is proposed as the key structure in the catalytic cycle, which is formed to release the induced strain. The optical properties of the ortho-terphenyl products have been measured as well as the coordination ability of Na+ and K+.

Harvard Citation style: Tran-Van, A., Götz, S., Neuburger, M. and Wegner, H. (2014) A Strain Induced Change of Mechanism from a [2+2+2] to a [2+1+2+1] Cycloaddition Reaction, Organic Letters, 16(9), pp. 2410-2413. https://doi.org/10.1021/ol5007604

APA Citation style: Tran-Van, A., Götz, S., Neuburger, M., & Wegner, H. (2014). A Strain Induced Change of Mechanism from a [2+2+2] to a [2+1+2+1] Cycloaddition Reaction. Organic Letters. 16(9), 2410-2413. https://doi.org/10.1021/ol5007604