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).
|Number of pages||4|
|Publication status||Published - 21 Apr 2015|