[4+2]-Cycloaddition of sterically hindered thiophene S-oxides to alkenes and SO extrusion reactions of the cycloadducts

Thies Thiemann; Jesus Iniesta; David J. Walton

doi:10.1080/10426507.2015.1100191

[4+2]-Cycloaddition of sterically hindered thiophene S-oxides to alkenes and SO extrusion reactions of the cycloadducts

Thies Thiemann, Jesus Iniesta, David J. Walton

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

6 Citations (Scopus)

Abstract

Cycloaddition reactions of 2,5-di-tert-butylthiophene S-oxide and 2,3,4,5-tetrakis(p-tolyl)thiophene S-oxide with alkenes are described. The reactivity of 2,5-di-tert-butylthiophene S-oxide as diene in Diels–Alder reactions is compared with 2,5-di-tert-butylthiophene S,S-dioxide. The thermal and photochemical SO extrusion reactions of the cycloadducts under formation of highly substitutedaromatic compounds are exemplified.

Original language	English
Pages (from-to)	876-884
Number of pages	9
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	191
Issue number	6
DOIs	https://doi.org/10.1080/10426507.2015.1100191
Publication status	Published - 2016
Externally published	Yes

Keywords

SO extrusion
Thiophene S,S-dioxide
cycloaddition
thiophene S-oxide

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

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10.1080/10426507.2015.1100191

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title = "[4+2]-Cycloaddition of sterically hindered thiophene S-oxides to alkenes and SO extrusion reactions of the cycloadducts",

abstract = "Cycloaddition reactions of 2,5-di-tert-butylthiophene S-oxide and 2,3,4,5-tetrakis(p-tolyl)thiophene S-oxide with alkenes are described. The reactivity of 2,5-di-tert-butylthiophene S-oxide as diene in Diels–Alder reactions is compared with 2,5-di-tert-butylthiophene S,S-dioxide. The thermal and photochemical SO extrusion reactions of the cycloadducts under formation of highly substitutedaromatic compounds are exemplified.",

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year = "2016",

doi = "10.1080/10426507.2015.1100191",

language = "English",

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pages = "876--884",

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T1 - [4+2]-Cycloaddition of sterically hindered thiophene S-oxides to alkenes and SO extrusion reactions of the cycloadducts

AU - Thiemann, Thies

AU - Iniesta, Jesus

AU - Walton, David J.

PY - 2016

Y1 - 2016

N2 - Cycloaddition reactions of 2,5-di-tert-butylthiophene S-oxide and 2,3,4,5-tetrakis(p-tolyl)thiophene S-oxide with alkenes are described. The reactivity of 2,5-di-tert-butylthiophene S-oxide as diene in Diels–Alder reactions is compared with 2,5-di-tert-butylthiophene S,S-dioxide. The thermal and photochemical SO extrusion reactions of the cycloadducts under formation of highly substitutedaromatic compounds are exemplified.

AB - Cycloaddition reactions of 2,5-di-tert-butylthiophene S-oxide and 2,3,4,5-tetrakis(p-tolyl)thiophene S-oxide with alkenes are described. The reactivity of 2,5-di-tert-butylthiophene S-oxide as diene in Diels–Alder reactions is compared with 2,5-di-tert-butylthiophene S,S-dioxide. The thermal and photochemical SO extrusion reactions of the cycloadducts under formation of highly substitutedaromatic compounds are exemplified.

KW - SO extrusion

KW - Thiophene S,S-dioxide

KW - cycloaddition

KW - thiophene S-oxide

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DO - 10.1080/10426507.2015.1100191

M3 - Article

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SP - 876

EP - 884

JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

IS - 6

ER -

[4+2]-Cycloaddition of sterically hindered thiophene S-oxides to alkenes and SO extrusion reactions of the cycloadducts

Abstract

Keywords

ASJC Scopus subject areas

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