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Hill-Cousins JT, Pop IA, Pileio G, et al. Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state. Org Lett. 2015;17(9):2150-3doi: 10.1021/acs.orglett.5b00744.
Hill-Cousins, J. T., Pop, I. A., Pileio, G., Stevanato, G., Håkansson, P., Roy, S. S., Levitt, M. H., Brown, L. J., & Brown, R. C. (2015). Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state. Organic letters, 17(9), 2150-3. https://doi.org/10.1021/acs.orglett.5b00744
Hill-Cousins, Joseph T, et al. "Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state." Organic letters vol. 17,9 (2015): 2150-3. doi: https://doi.org/10.1021/acs.orglett.5b00744
Hill-Cousins JT, Pop IA, Pileio G, Stevanato G, Håkansson P, Roy SS, Levitt MH, Brown LJ, Brown RC. Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state. Org Lett. 2015 May 01;17(9):2150-3. doi: 10.1021/acs.orglett.5b00744. Epub 2015 Apr 21. PMID: 25898076; PMCID: PMC4516318.
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Org Lett. 2015 May 01;17(9):2150-3. doi: 10.1021/acs.orglett.5b00744. Epub 2015 Apr 21.

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

Organic letters

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

Affiliations

  1. Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K.

PMID: 25898076 PMCID: PMC4516318 DOI: 10.1021/acs.orglett.5b00744

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 (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.

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