Unprecedented pseudo-ortho and ortho metallation of [2.2]paracyclophanes--a methyl group matters

Mirja Enders; Christian J Friedmann; Philipp N Plessow; Angela Bihlmeier; Martin Nieger; Wim Klopper; Stefan Bräse

doi:10.1039/c5cc00492f

Unprecedented pseudo-ortho and ortho metallation of [2.2]paracyclophanes--a methyl group matters

Chem Commun (Camb). 2015 Mar 21;51(23):4793-5. doi: 10.1039/c5cc00492f.

Authors

Mirja Enders¹, Christian J Friedmann, Philipp N Plessow, Angela Bihlmeier, Martin Nieger, Wim Klopper, Stefan Bräse

Affiliation

¹ Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany. braese@kit.edu.

PMID: 25692386
DOI: 10.1039/c5cc00492f

Abstract

The first example of a pseudo-ortho metallation on [2.2]paracyclophane is presented, giving easy access to enantiopure compounds of this type. By slight modification of the directing group, metallation of the ortho- and C2-positions is possible. The mechanism was further investigated by means of density functional theory (DFT) calculations.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Metals / chemistry*
Models, Molecular
Molecular Structure
Polycyclic Compounds / chemical synthesis
Polycyclic Compounds / chemistry*

Substances

Metals
Polycyclic Compounds
(2.2)paracyclophane