Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state.

Autor: Hill-Cousins JT; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Pop IA; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Pileio G; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Stevanato G; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Håkansson P; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Roy SS; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Levitt MH; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Brown LJ; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K., Brown RC; Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2015 May 01; Vol. 17 (9), pp. 2150-3. Date of Electronic Publication: 2015 Apr 21.
DOI: 10.1021/acs.orglett.5b00744
Abstrakt: The synthesis of an octa-alkoxy substituted isotopically labeled naphthalene derivative, shown to have excellent properties in singlet NMR experiments, is described. This highly substituted naphthalene system, which incorporates an adjacent (13)C spin pair, is readily accessed from a commercially available (13)C2-labeled building block via sequential thermal alkynyl- and arylcyclobutenone rearrangements. The synthetic route incorporates a simple desymmetrization approach leading to a small difference in the chemical shifts of the (13)C spin pair, a design constraint crucial for accessing nuclear singlet order.
Databáze: MEDLINE