Alkyl substituted [2.2]paracyclophane-1,9-dienes?

Organic & Biomolecular Chemistry Pub Date: 2016-06-01 DOI: 10.1039/C6OB00885B

Abstract

[2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.

Graphical abstract: Alkyl substituted [2.2]paracyclophane-1,9-dienes
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