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

T. Thiemann; J. Iniesta; David 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

T. Thiemann, J. Iniesta, David Walton

School of Health and Care

Research output: Contribution to journal › Article

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
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

Keywords

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

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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.",

keywords = "Thiophene S, S-dioxide, thiophene S-oxide, cycloaddition, SO extrusion",

author = "T. Thiemann and J. Iniesta and David Walton",

year = "2016",

doi = "10.1080/10426507.2015.1100191",

language = "English",

volume = "191",

pages = "876--884",

journal = "Phosphorus, Sulfur, and Silicon and the Related Elements",

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TY - JOUR

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

AU - Thiemann, T.

AU - Iniesta, J.

AU - Walton, David

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 - Thiophene S

KW - S-dioxide

KW - thiophene S-oxide

KW - cycloaddition

KW - SO extrusion

U2 - 10.1080/10426507.2015.1100191

DO - 10.1080/10426507.2015.1100191

M3 - Article

SN - 1042-6507

SN - 1563-5325

VL - 191

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

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