University of Sussex
Browse

File(s) not publicly available

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

journal contribution
posted on 2023-06-07, 23:06 authored by Rakesh Parmar, Martyn P Coles, Peter B Hitchcock, Gareth J Rowlands
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.

History

Publication status

  • Published

Journal

Synthesis

ISSN

00397881

Issue

24

Volume

-

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

Usage metrics

    University of Sussex (Publications)

    Categories

    No categories selected

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC