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

doi:10.1021/acs.orglett.5b00744

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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

Original language	English
Pages (from-to)	2150-2153
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.5b00744
Publication status	Published - 21 Apr 2015

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title = "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 13C spin pair, is readily accessed from a commercially available 13C2-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 13C spin pair, a design constraint crucial for accessing nuclear singlet order. (Chemical Equation Presented).",

author = "Hill-Cousins, {Joseph T.} and Pop, {Ionut Alexandru} and Giuseppe Pileio and Gabriele Stevanato and P{\"a}r H{\aa}kansson and Roy, {Soumya S.} and Levitt, {Malcolm H.} and Brown, {Lynda J.} and Brown, {Richard C D}",

year = "2015",

month = apr,

day = "21",

doi = "10.1021/acs.orglett.5b00744",

language = "English",

volume = "17",

pages = "2150--2153",

journal = "Organic Letters",

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TY - JOUR

T1 - Synthesis of an Isotopically Labeled Naphthalene Derivative That Supports a Long-Lived Nuclear Singlet State

AU - Hill-Cousins, Joseph T.

AU - Pop, Ionut Alexandru

AU - Pileio, Giuseppe

AU - Stevanato, Gabriele

AU - Håkansson, Pär

AU - Roy, Soumya S.

AU - Levitt, Malcolm H.

AU - Brown, Lynda J.

AU - Brown, Richard C D

PY - 2015/4/21

Y1 - 2015/4/21

N2 - 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 13C spin pair, is readily accessed from a commercially available 13C2-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 13C spin pair, a design constraint crucial for accessing nuclear singlet order. (Chemical Equation Presented).

AB - 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 13C spin pair, is readily accessed from a commercially available 13C2-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 13C spin pair, a design constraint crucial for accessing nuclear singlet order. (Chemical Equation Presented).

UR - http://www.scopus.com/inward/record.url?scp=84928884135&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b00744

DO - 10.1021/acs.orglett.5b00744

M3 - Article

AN - SCOPUS:84928884135

VL - 17

SP - 2150

EP - 2153

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 9

ER -

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

Abstract

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