Cyclic Sulfones. VII. The Dimerization of 3,4-Diphenylthiophene 1,1-Dioxide<sup>1</sup>

Overberger, C. G.; Whelan, John M.

doi:10.1021/jo01069a035

Cited by 11 publications

(2 citation statements)

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“…406. H 209.45/ Piperidine (9) 404.58 226.8/ Pyrrolidine (10) 404.60 223.3# Pyridine (11) 404.82 220.9/ Aniline (12) 405.31 211.2/ /V-Monomethylaniline (13) 405.01 217.4/ /V,/V-Dimethylaniline (14) 405.06 224.0/ Cyclohexylamine (15) 404.72 222.0/ Formamide (16) 406.30 /V-Monomethylforma- number of gaseous amines extending previous data6"8 to these systems wherein the site of protonation may be ambiguous. The data (Table I) were obtained with a McPherson ESCA-36 instrument on gaseous samples of the amines at ~100-µ pressure intimately mixed with similar amounts of Ar for calibration.9 The Mg x ray was used for excitation.…”

Section: Department Of Chemical Engineeringmentioning

confidence: 99%

Hydrogenation of 1,3-butadiene with 1,3-cyclohexadiene and molecular deuterium over zirconium dioxide catalysts

Yamaguchi¹,

Hightower²

1977

J. Am. Chem. Soc.

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Section: Department Of Chemical Engineeringmentioning

confidence: 99%

Hydrogenation of 1,3-butadiene with 1,3-cyclohexadiene and molecular deuterium over zirconium dioxide catalysts

Yamaguchi¹,

Hightower²

1977

J. Am. Chem. Soc.

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“…[1,2] Although applications of thiophenes in Diels-Alder reactions have been described, [3] am ore common way to use thiophenes as dienes is after oxidation to the corresponding thiopheneS ,S-dioxides. [4] Although non-stabilized thiophene dioxides easily undergod imerizationr eactions, [5,6] their stabilized analogues are used as dienes in cycloadditions with alkenes [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] and alkynes, [22][23][24][25][26][27] mostly under drastic reactionc onditions. However,t he oxidation of thiophenes can be stoppeda tt he sulfoxide stage and the resulting thiopheneS -oxides undergo Diels-Alder reactions under much milder conditions.…”

Section: Introductionmentioning

confidence: 99%

Towards the Design of Optically Active Thiophene S‐Oxides using Quantum Chemistry

Verlinden

Woller

Proft

et al. 2019

Chemistry A European J

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The importance of axially chiral biaryls has risen steeply in the recent decades. This structural motif proved to be successful in catalytic asymmetric synthesis and the configuration of the biaryl axis is decisive for the biological activity. A new approach for the atroposelective synthesis of biaryls would be through a cycloaddition between an enantiopure phenyl‐substituted thiophene S‐oxide and an alkyne. Importantly, the chiral center of the thiophene S‐oxide needs to be stable enough to avoid pyramidal inversion during the cycloaddition. Considering that the racemization of thiophene monoxides has been scarcely investigated so far, we perform a thorough quantum chemical study on the inversion barriers of a large number of chiral thiophene S‐oxide derivatives. Our main goal is to identify substitution patterns leading to stable atropisomers at room temperature. Appealingly, the role of stereoelectronic effects and the position of the substituents as well as the importance of aromaticity on the pyramidal inversion barrier are elucidated for the first time.

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Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Guziec

2022

Organic Reactions

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Extrusion reactions may be defined as chemical reactions in which an atom or small molecular fragment Y connected to two other atoms W and Z is lost from a molecule, leading to a product in which W becomes directly bonded to Z. Cheletropic reactions that afford aromatic or conjugated π systems by loss of a stable atomic or molecular fragment have also been classified as extrusion reactions. Typically, the fragments liberated in these reactions are small, stable inorganic molecules or atoms such as carbon monoxide, carbon dioxide, sulfur, sulfur monoxide, sulfur dioxide, selenium, tellurium, oxygen and nitrogen. This chapter primarily deals with the synthesis of arenes, heterocycles, 1,3‐dienes and polyenes using such extrusion processes. The utility of these reactions in the synthesis of sterically hindered molecules, dendrimers, pheromones, and other natural products are highlighted. The use of extrusion reactions for the “Click and Release” approach in drug development is also introduced.

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Cyclic Sulfones. VII. The Dimerization of 3,4-Diphenylthiophene 1,1-Dioxide¹

Cited by 11 publications

References 0 publications

Hydrogenation of 1,3-butadiene with 1,3-cyclohexadiene and molecular deuterium over zirconium dioxide catalysts

Hydrogenation of 1,3-butadiene with 1,3-cyclohexadiene and molecular deuterium over zirconium dioxide catalysts

Towards the Design of Optically Active Thiophene S‐Oxides using Quantum Chemistry

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

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Cyclic Sulfones. VII. The Dimerization of 3,4-Diphenylthiophene 1,1-Dioxide1

Cited by 11 publications

References 0 publications

Hydrogenation of 1,3-butadiene with 1,3-cyclohexadiene and molecular deuterium over zirconium dioxide catalysts

Hydrogenation of 1,3-butadiene with 1,3-cyclohexadiene and molecular deuterium over zirconium dioxide catalysts

Towards the Design of Optically Active Thiophene S‐Oxides using Quantum Chemistry

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

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Cyclic Sulfones. VII. The Dimerization of 3,4-Diphenylthiophene 1,1-Dioxide¹