Synthesis of an Isotopically Labeled Naphthalene Derivative That Supports a Long-Lived Nuclear Singlet State

Joseph T. Hill-Cousins*, Ionut Alexandru Pop, Giuseppe Pileio, Gabriele Stevanato, Pär Håkansson, Soumya S. Roy, Malcolm H. Levitt, Lynda J. Brown, Richard C D Brown

*Corresponding author for this work

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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 <sup>13</sup>C spin pair, is readily accessed from a commercially available <sup>13</sup>C<inf>2</inf>-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 <sup>13</sup>C spin pair, a design constraint crucial for accessing nuclear singlet order. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)2150-2153
Number of pages4
JournalOrganic Letters
Issue number9
Publication statusPublished - 21 Apr 2015

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