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

Letter. Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state
Letter. Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state
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.
1523-7060
2150-2153
Hill-Cousins, Joseph
52574106-db8c-4f0c-85ed-e388710fe723
Pop, Ionut-Alexandru
fb310398-c5e3-4942-96de-a95354adafc4
Pileio, Giuseppe
13f78e66-0707-4438-b9c9-6dbd3eb7d4e8
Stevanato, Gabriele
13f2e0a2-2ce7-4938-a2ac-274a81196a72
Hakansson, Par
814e08b5-ae95-408f-a669-bec9c0ef4235
Singha Roy, Soumya
fa8b7e87-8477-417a-932e-61e36581c720
Levitt, Malcolm
bcc5a80a-e5c5-4e0e-9a9a-249d036747c3
Brown, Lynda
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Brown, Richard
21ce697a-7c3a-480e-919f-429a3d8550f5
Hill-Cousins, Joseph
52574106-db8c-4f0c-85ed-e388710fe723
Pop, Ionut-Alexandru
fb310398-c5e3-4942-96de-a95354adafc4
Pileio, Giuseppe
13f78e66-0707-4438-b9c9-6dbd3eb7d4e8
Stevanato, Gabriele
13f2e0a2-2ce7-4938-a2ac-274a81196a72
Hakansson, Par
814e08b5-ae95-408f-a669-bec9c0ef4235
Singha Roy, Soumya
fa8b7e87-8477-417a-932e-61e36581c720
Levitt, Malcolm
bcc5a80a-e5c5-4e0e-9a9a-249d036747c3
Brown, Lynda
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Brown, Richard
21ce697a-7c3a-480e-919f-429a3d8550f5

Hill-Cousins, Joseph, Pop, Ionut-Alexandru, Pileio, Giuseppe, Stevanato, Gabriele, Hakansson, Par, Singha Roy, Soumya, Levitt, Malcolm, Brown, Lynda and Brown, Richard (2015) Letter. Synthesis of an isotopically labeled naphthalene derivative that supports a long-lived nuclear singlet state. Organic Letters, 17 (9), 2150-2153. (doi:10.1021/acs.orglett.5b00744).

Record type: Article

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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e-pub ahead of print date: 21 April 2015
Published date: 1 May 2015
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Magnetic Resonance

Identifiers

Local EPrints ID: 395470
URI: https://eprints.soton.ac.uk/id/eprint/395470
ISSN: 1523-7060
PURE UUID: bc3a0d65-213c-4956-957f-f920e9822db0
ORCID for Giuseppe Pileio: ORCID iD orcid.org/0000-0001-9223-3896
ORCID for Malcolm Levitt: ORCID iD orcid.org/0000-0001-9878-1180
ORCID for Lynda Brown: ORCID iD orcid.org/0000-0002-5678-0814
ORCID for Richard Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 31 May 2016 10:34
Last modified: 14 Jul 2018 00:35

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