☆ 4.6 Article

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

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY

Volume 14, Issue 25, Pages 6079-6087

Publisher

ROYAL SOC CHEMISTRY

DOI: 10.1039/c6ob00885b

Keywords

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Categories

Chemistry, Organic

Funding

EPSRC [EP/F056397/1] Funding Source: UKRI
Engineering and Physical Sciences Research Council [975544, EP/F056397/1] Funding Source: researchfish

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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-(tri-methylsilyl) 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.

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