Synthesis and Diels–Alder reactions of electron deficient 2,3-ethylenedisulphonyl-1,3-butadiene

Lee, Shwu-Jiuan; Lee, Jui-Chen; Peng, Man-Li; Chou, Teh‐Chang

doi:10.1039/c39890001020

Cited by 23 publications

(5 citation statements)

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“…The introduction of hetero substituents has a significant influence on the reactivity and regioselectivity of the diene. 18 According to Table III, compound 11 is more stable than 9 and 10. Cook and Tonge suggested that intramolecular dipole-dipole interactions contribute in some measure to the observed stabilization.…”

Section: Tetroxo-mentioning

confidence: 96%

An Ab Initio Study of Conformational Energies in Dioxo-, Trioxo-, and Tetroxo-Dithianes

Yavari

Amiri

Haghdadi

2006

Phosphorus, Sulfur, and Silicon and the Related Elements

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Section: Tetroxo-mentioning

confidence: 96%

An Ab Initio Study of Conformational Energies in Dioxo-, Trioxo-, and Tetroxo-Dithianes

Yavari

Amiri

Haghdadi

2006

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…Chou and co-workers developed an elegant synthesis of a 1,4-dithiane-fused sulfolane 45 ( Scheme 9b ) [ 56 ]. Oxidation of the 1,4-dithiane-fused sulfolane 44 to the hexoxide and heating to 130 °C afforded the pure 1,4-dithiane-tethered diene 45 via the usual retro-chelotropic reaction of sulfolanes.…”

Section: Reviewmentioning

confidence: 99%

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

Ryckaert¹,

Demeyere²,

Degroote³

et al. 2023

Beilstein J. Org. Chem.

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This review covers the synthetic applications of 1,4-dithianes, as well as derivatives thereof at various oxidation states. The selected examples show how the specific heterocyclic reactivity can be harnessed for the controlled synthesis of carbon–carbon bonds. The reactivity is compared to and put into context with more common synthetic building blocks, such as 1,3-dithianes and (hetero)aromatic building blocks. 1,4-Dithianes have as yet not been investigated to the same extent as their well-known 1,3-dithiane counterparts, but they do offer attractive transformations that can find good use in the assembly of a wide array of complex molecular architectures, ranging from lipids and carbohydrates to various carbocyclic scaffolds. This versatility arises from the possibility to chemoselectively cleave or reduce the sulfur-heterocycle to reveal a versatile C2-synthon.

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“…However, 137 behaved with dual electron demand and reacted regio- and stereoselectively with both electron-rich and electron-deficient dienophiles . The cyclic 2,3-bis(sulfonyl)diene 138 was designed to overcome the lower reactivity of 130 caused by the preferred transoid conformation of the latter and also cycloadded to both types of dienophiles . The α-vinyl and γ-vinyl allenic sulfones 139 and 140 , respectively, as well as their sulfoxide analogs, underwent [4 + 2] cycloadditions, followed by [1,5] hydrogen shifts to afford the corresponding arenes (Scheme ).…”

Section: Diels−alder Cycloadditionsmentioning

confidence: 99%

Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones

2010

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Introduction 4499 2. Diels-Alder Cycloadditions 4499 2.1. Unsaturated Sulfones as Dienophiles 4499 2.1.1. Early Studies 4499 2.1.2. Aromatization of Cycloaddition Products of Acetylenic Sulfones 4501 2.1.3. Iterative Diels-Alder and Ramberg-Backlund Reactions of Chloroalkylsulfonyl Allenes 4502 2.1.4. Diels-Alder Cycloadditions of Bis(sulfonyl)acetylenes and Their Equivalents 4502 2.1.5. Diels-Alder Cycloadditions of Acetylenic Sulfones Containing Heteroatom Substituents 4503 2.1.6. Diels-Alder Reactions of Dienyl Sulfones as Dienophiles 4504 2.1.7. Diels-Alder Reactions of Unsaturated Sulfones with Pyrroles 4505 2.1.8. Diels-Alder Reactions of Unsaturated Sulfones with Furans and Isobenzofurans 4507 2.1.9. Miscellaneous Cycloadditions 4508 2.2. Dienyl Sulfones As the Diene Components in Diels-Alder Reactions 4509 2.2.1. 1-Sulfonyl Derivatives † Dedicated to Professor David N. Harpp, for his inspiring contributions as a teacher, mentor and scholar.

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Synthesis and Diels–Alder reactions of electron deficient 2,3-ethylenedisulphonyl-1,3-butadiene

Cited by 23 publications

References 0 publications

An Ab Initio Study of Conformational Energies in Dioxo-, Trioxo-, and Tetroxo-Dithianes

An Ab Initio Study of Conformational Energies in Dioxo-, Trioxo-, and Tetroxo-Dithianes

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones

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