Issue 14, 2011

Mild preparation of functionalized [2.2]paracyclophanes via the Pummerer rearrangement

Abstract

[2.2]Paracyclophanes, incorporating functional groups in the aliphatic bridges, suitable for elimination to give [2.2]paracyclophanedienes, are synthesized through a novel approach. It relies on a double Pummerer rearrangement on dithiacyclophane precursors, followed by ring contraction through a photochemical sulfur extrusion, and it is compatible with aryl moieties possessing very different electronic properties.

Graphical abstract: Mild preparation of functionalized [2.2]paracyclophanes via the Pummerer rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
27 Feb 2011
Accepted
31 Mar 2011
First published
31 Mar 2011

Org. Biomol. Chem., 2011,9, 5018-5020

Mild preparation of functionalized [2.2]paracyclophanes via the Pummerer rearrangement

M. Montanari, A. Bugana, A. K. Sharma and D. Pasini, Org. Biomol. Chem., 2011, 9, 5018 DOI: 10.1039/C1OB05319A

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