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

Abstract

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 C-13 spin pair, is readily accessed from a commercially available C-13(2)-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 C-13 spin pair, a design constraint crucial for accessing nuclear singlet order.

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