Sulfur monoxide: generation, trapping, and synthetic applications

Connor Prior; Richard S. Grainger

doi:10.1016/B978-0-443-18939-5.00014-7

Sulfur monoxide: generation, trapping, and synthetic applications

Connor Prior, Richard S. Grainger^*

^*Corresponding author for this work

Chemistry

Research output: Chapter in Book/Report/Conference proceeding › Chapter

Abstract

Sulfur monoxide (SO) is an attractive building block for synthetic chemistry, offering the opportunity to directly introduce a sulfinyl group into an organic or inorganic compound. However, the rapid disproportionation of SO precludes its storage and direct use in synthesis. Methods for the in situ generation and trapping of both ground-state triplet and excited-state singlet SO are reviewed, along with cases involving formal loss and transfer of SO, but which do not involve free SO. Current limitations and synthetic opportunities are highlighted.

Original language	English
Title of host publication	Progress in Heterocyclic Chemistry
Editors	Gordon W. Gribble, R Alan Aitken
Publisher	Elsevier
Chapter	1
Pages	1-34
Number of pages	34
Edition	1st
ISBN (Electronic)	9780443189401
ISBN (Print)	9780443189395
DOIs	https://doi.org/10.1016/B978-0-443-18939-5.00014-7
Publication status	Published - 10 Jan 2023

Publication series

Name	Progress in Heterocyclic Chemistry
Publisher	Elsevier
Volume	34
ISSN (Print)	0959-6380
ISSN (Electronic)	2542-680X

Bibliographical note

Funding Information:
We thank the EPSRC (EP/C543130/1, EP/C543122/1) and the Leverhulme Trust (RPG-2017-260) for funding our own research into small molecule transfer reagents from 1,8-peri-substituted naphthalenes and related strained ring systems.

Publisher Copyright:
© 2023 Elsevier Inc.

Keywords

Aromaticity
Metal complexes
Ring strain
Sulfines
Sulfoxides
Sulfur heterocycles

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1016/B978-0-443-18939-5.00014-7

Controlled release of reactive di- and triatomic molecules
Grainger, R.
Leverhulme Trust
1/10/17 → 30/04/21
Project: Research
Harnessing Reactive Intermediates for Organic Synthesis
Grainger, R.
Engineering & Physical Science Research Council
1/10/05 → 31/03/09
Project: Research Councils
Advanced Research Fellowship: Harnessing Reactive Intermediates for Organic Synthesis
Grainger, R.
Engineering & Physical Science Research Council
1/09/05 → 31/08/10
Project: Research Councils

Cite this

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title = "Sulfur monoxide: generation, trapping, and synthetic applications",

abstract = "Sulfur monoxide (SO) is an attractive building block for synthetic chemistry, offering the opportunity to directly introduce a sulfinyl group into an organic or inorganic compound. However, the rapid disproportionation of SO precludes its storage and direct use in synthesis. Methods for the in situ generation and trapping of both ground-state triplet and excited-state singlet SO are reviewed, along with cases involving formal loss and transfer of SO, but which do not involve free SO. Current limitations and synthetic opportunities are highlighted.",

keywords = "Aromaticity, Metal complexes, Ring strain, Sulfines, Sulfoxides, Sulfur heterocycles",

author = "Connor Prior and Grainger, {Richard S.}",

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T1 - Sulfur monoxide

T2 - generation, trapping, and synthetic applications

AU - Prior, Connor

AU - Grainger, Richard S.

N1 - Funding Information: We thank the EPSRC (EP/C543130/1, EP/C543122/1) and the Leverhulme Trust (RPG-2017-260) for funding our own research into small molecule transfer reagents from 1,8-peri-substituted naphthalenes and related strained ring systems. Publisher Copyright: © 2023 Elsevier Inc.

PY - 2023/1/10

Y1 - 2023/1/10

N2 - Sulfur monoxide (SO) is an attractive building block for synthetic chemistry, offering the opportunity to directly introduce a sulfinyl group into an organic or inorganic compound. However, the rapid disproportionation of SO precludes its storage and direct use in synthesis. Methods for the in situ generation and trapping of both ground-state triplet and excited-state singlet SO are reviewed, along with cases involving formal loss and transfer of SO, but which do not involve free SO. Current limitations and synthetic opportunities are highlighted.

AB - Sulfur monoxide (SO) is an attractive building block for synthetic chemistry, offering the opportunity to directly introduce a sulfinyl group into an organic or inorganic compound. However, the rapid disproportionation of SO precludes its storage and direct use in synthesis. Methods for the in situ generation and trapping of both ground-state triplet and excited-state singlet SO are reviewed, along with cases involving formal loss and transfer of SO, but which do not involve free SO. Current limitations and synthetic opportunities are highlighted.

KW - Aromaticity

KW - Metal complexes

KW - Ring strain

KW - Sulfines

KW - Sulfoxides

KW - Sulfur heterocycles

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SN - 9780443189395

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BT - Progress in Heterocyclic Chemistry

A2 - Gribble, Gordon W.

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ER -

Sulfur monoxide: generation, trapping, and synthetic applications

Abstract

Publication series

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Projects

Controlled release of reactive di- and triatomic molecules

Harnessing Reactive Intermediates for Organic Synthesis

Advanced Research Fellowship: Harnessing Reactive Intermediates for Organic Synthesis

Cite this