Towards a flexible strategy for the synthesis of enantiomerically pure [2.2]paracyclophane derivatives: The chemistry of 4-tolylsulfinyl[2.2] paracyclophane

Parmar, Rakesh, Coles, Martyn P, Hitchcock, Peter B and Rowlands, Gareth J (2010) Towards a flexible strategy for the synthesis of enantiomerically pure [2.2]paracyclophane derivatives: The chemistry of 4-tolylsulfinyl[2.2] paracyclophane. Synthesis, - (24). ISSN 00397881

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Abstract

The use of enantiomerically enriched 4-tolylsulfinyl[2.2]paracyclophane as a precursor to a variety of mono- and di-substituted [2.2]paracyclophane derivatives is described. The goal of our research is to develop a single general precursor that permits the synthesis of the most common [2.2]paracyclophane substitution patterns. The chemistry of two diastereoisomers of 4-tolylsulfinyl[2.2]paracyclophane has been explored and it facilitates the synthesis of enantiomerically enriched 4-substituted and 4,13-disubstituted [2.2]paracyclophanes. Directed lithiations result in an unusual cyclisation reaction. Whilst the tolyl group cannot realise our goal, the chemistry outlined acts as a successful proof of concept.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Martyn Coles
Date Deposited: 06 Feb 2012 19:30
Last Modified: 23 Mar 2012 09:21
URI: http://sro.sussex.ac.uk/id/eprint/20885
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