Azulenesulfonium and azulenebis(sulfonium) salts: Formation by interrupted Pummerer reaction and subsequent derivatisation by nucleophiles

Carlos M. López-Alled; Frederick J.O. Martin; Kuan Yu Chen; Gabriele Kociok-Köhn; Tony D. James; Jannis Wenk; Simon E. Lewis

doi:10.1016/j.tet.2020.131700

Azulenesulfonium and azulenebis(sulfonium) salts: Formation by interrupted Pummerer reaction and subsequent derivatisation by nucleophiles

Carlos M. López-Alled, Frederick J.O. Martin, Kuan Yu Chen, Gabriele Kociok-Köhn, Tony D. James, Jannis Wenk, Simon E. Lewis

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Abstract

Azulenes undergo either single or dual S_EAr reactions depending on the nature of the sulfur(IV) electrophile employed. These electrophiles are generated in situ from either sulfoxides or sulfides. The resultant cationic or dicationic azulene products can undergo further derivatisation by means of nucleophilic attack at the sulfonium α-carbon. In the case of cycloalkyl azulenylsulfonium salts, this leads to ring-opened azulenylsulfide products.

This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No 665992

Original language	English
Article number	131700
Journal	Tetrahedron
Volume	76
Issue number	49
Early online date	22 Oct 2020
DOIs	https://doi.org/10.1016/j.tet.2020.131700
Publication status	Published - 4 Dec 2020

Funding

We are grateful for PhD funding to C.M.L.-A. from the EU Horizon 2020 research and innovation programme under grant agreement H2020-MSCA-CO-FUND , # 665992 . The Centre for Sustainable Chemical Technologies is supported by EPSRC under grant EP/L016354/1 . T.D.J. thanks the Royal Society for a Wolfson Research Merit Award. The British-Spanish Society and Plastic Energy are thanked for a 2017 Scholarship to C. M. L.-A. NMR and X-ray crystallography facilities were provided through the Materials and Chemical Characterization (MC 2 ) Facility at the University of Bath.

Keywords

Azulene
Interrupted Pummerer
Sulfonium

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1016/j.tet.2020.131700

___Tetrahedron_2020_76_131700___Final published version, 2.73 MBLicence: CC BY

Cite this

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title = "Azulenesulfonium and azulenebis(sulfonium) salts: Formation by interrupted Pummerer reaction and subsequent derivatisation by nucleophiles",

abstract = "Azulenes undergo either single or dual SEAr reactions depending on the nature of the sulfur(IV) electrophile employed. These electrophiles are generated in situ from either sulfoxides or sulfides. The resultant cationic or dicationic azulene products can undergo further derivatisation by means of nucleophilic attack at the sulfonium α-carbon. In the case of cycloalkyl azulenylsulfonium salts, this leads to ring-opened azulenylsulfide products.This project has received funding from the European Union{\textquoteright}s Horizon 2020 research and innovation programme under the Marie Sk{\l}odowska-Curie grant agreement No 665992 ",

keywords = "Azulene, Interrupted Pummerer, Sulfonium",

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T2 - Formation by interrupted Pummerer reaction and subsequent derivatisation by nucleophiles

AU - López-Alled, Carlos M.

AU - Martin, Frederick J.O.

AU - Chen, Kuan Yu

AU - Kociok-Köhn, Gabriele

AU - James, Tony D.

AU - Wenk, Jannis

AU - Lewis, Simon E.

PY - 2020/12/4

Y1 - 2020/12/4

N2 - Azulenes undergo either single or dual SEAr reactions depending on the nature of the sulfur(IV) electrophile employed. These electrophiles are generated in situ from either sulfoxides or sulfides. The resultant cationic or dicationic azulene products can undergo further derivatisation by means of nucleophilic attack at the sulfonium α-carbon. In the case of cycloalkyl azulenylsulfonium salts, this leads to ring-opened azulenylsulfide products.This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No 665992

AB - Azulenes undergo either single or dual SEAr reactions depending on the nature of the sulfur(IV) electrophile employed. These electrophiles are generated in situ from either sulfoxides or sulfides. The resultant cationic or dicationic azulene products can undergo further derivatisation by means of nucleophilic attack at the sulfonium α-carbon. In the case of cycloalkyl azulenylsulfonium salts, this leads to ring-opened azulenylsulfide products.This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No 665992

KW - Azulene

KW - Interrupted Pummerer

KW - Sulfonium

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DO - 10.1016/j.tet.2020.131700

M3 - Article

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JO - Tetrahedron

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Azulenesulfonium and azulenebis(sulfonium) salts: Formation by interrupted Pummerer reaction and subsequent derivatisation by nucleophiles

Abstract

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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Avance NEO 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Dual source (Cu and Mo) Single Crystal Diffractometer (SuperNova)

Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

Cite this

Azulenesulfonium and azulenebis(sulfonium) salts: Formation by interrupted Pummerer reaction and subsequent derivatisation by nucleophiles

Abstract

Funding

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Equipment

Avance NEO 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Dual source (Cu and Mo) Single Crystal Diffractometer (SuperNova)

Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

Cite this