Alkyl substituted [2.2]paracyclophane-1, 9-dienes. Issue 25 (1st June 2016)

• Record Type: Journal Article
• Authors: Lidster, Benjamin J.; Kumar, Dharam R.; Spring, Andrew M.; Yu, Chin-Yang; Helliwell, Madeleine; Raftery, James; Turner, Michael L.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 25(2016)
• Page Start: 6079
• Page End: 6087
• Publication Date: 2016-06-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00885b
• Languages: English
• ISSNs: 1477-0520

Abstract

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.