Alkyl substituted [2.2]paracyclophane-1, 9-dienes. Issue 25 (1st June 2016) - Lidster, Benjamin J.
Abstract : Highly strained alkyl-substituted [2.2]paracyclophane-1, 9-dienes, suitable for ring opening metathesis polymerization to poly(phenylene vinylenes), have been prepared in excellent yields. 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.