Strathprints logo
Strathprints Home | Open Access | Browse | Search | User area | Copyright | Help | Library Home | SUPrimo

Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction : regiochemical control via the phenylsulfonyl group

Crowley, Patrick J and Fawcett, John and Griffith, Gerry A and Moralee, Andrew C and Percy, Jonathan and Salafia, Vittoria (2005) Highly-functionalised difluorinated cyclohexane polyols via the Diels–Alder reaction : regiochemical control via the phenylsulfonyl group. Organic and biomolecular chemistry (18). pp. 3297-3310. ISSN 1477-0520

[img]
Preview
PDF
highly_functionalised_difluorinated.pdf - Published Version

Download (509kB) | Preview

Abstract

A difluorinated dienophile underwent cycloaddition reactions with a range of furans to afford cycloadducts whichcould be processed regio- and stereoselectively via episulfonium ions, generated by the reaction between their alkenyl groups and phenylsulfenyl chloride. The oxabicyclic products were oxidised to the phenylsulfonyl level and ring opened via E1CB or reductive desulfonative pathways to afford, ultimately, difluorinated cyclohexene or cyclohexane polyols.

Item type: Article
ID code: 40325
Keywords: cyclohexane polyols , Diels–Alder reaction , phenylsulfonyl group, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Depositing user: Pure Administrator
Date Deposited: 03 Jul 2012 13:05
Last modified: 21 May 2015 14:29
URI: http://strathprints.strath.ac.uk/id/eprint/40325

Actions (login required)

View Item View Item