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Literature DB >> 17668103

Sulfonyl vs. carbonyl group: which is the more electron-withdrawing?

Isabelle Chataigner¹, Cécilia Panel, Hélène Gérard, Serge R Piettre.

Abstract

Unexpectedly high reactivity of nitrogenated aromatics protected as amides or carbamates, when compared to sulfonamides, can be explained by a decrease of the aromaticity due to a greater ability of the carbon-centered groups to achieve delocalisation of the nitrogen lone pair, resulting in stronger global withdrawing effects.

Entities: Chemical

Year: 2007 PMID： 17668103 DOI： 10.1039/b705034h

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

7 in total

1. Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Authors: Thomas P Willumstad; Olesya Haze; Xiao Yin Mak; Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal: J Org Chem Date: 2013-10-28 Impact factor: 4.354

2. Photocatalytic Indole Diels-Alder Cycloadditions Mediated by Heterogeneous Platinum-Modified Titanium Dioxide.

Authors: Spencer P Pitre; Juan C Scaiano; Tehshik P Yoon
Journal: ACS Catal Date: 2017-08-11 Impact factor: 13.084

3. The effect of the intramolecular C-H⋯O interactions on the conformational preferences of bis-arylsulfones - 5-HT₆ receptor antagonists and beyond.

Authors: Justyna Kalinowska-Tłuścik; Jakub Staroń; Anna Krawczuk; Stefan Mordalski; Dawid Warszycki; Grzegorz Satała; Adam S Hogendorf; Andrzej J Bojarski
Journal: RSC Adv Date: 2018-05-22 Impact factor: 4.036

7. Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water.

Authors: Sadhan Jana; Ajay Verma; Rahul Kadu; Sangit Kumar
Journal: Chem Sci Date: 2017-07-10 Impact factor: 9.825

7 in total

Sulfonyl vs. carbonyl group: which is the more electron-withdrawing?

1. Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

2. Photocatalytic Indole Diels-Alder Cycloadditions Mediated by Heterogeneous Platinum-Modified Titanium Dioxide.

3. The effect of the intramolecular C-H⋯O interactions on the conformational preferences of bis-arylsulfones - 5-HT₆ receptor antagonists and beyond.

Review 4. An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects.

5. Highly Selective and Catalytic C-N Bond Cleavage of Tertiary Sulfonamides: Scope and Mechanistic Insight.

6. Azanorbornadienes as Thiol-Reactive Cleavable Linkers.

7. Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water.

Sulfonyl vs. carbonyl group: which is the more electron-withdrawing?

1. Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

2. Photocatalytic Indole Diels-Alder Cycloadditions Mediated by Heterogeneous Platinum-Modified Titanium Dioxide.

3. The effect of the intramolecular C-H⋯O interactions on the conformational preferences of bis-arylsulfones - 5-HT6 receptor antagonists and beyond.

Review 4. An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects.

5. Highly Selective and Catalytic C-N Bond Cleavage of Tertiary Sulfonamides: Scope and Mechanistic Insight.

6. Azanorbornadienes as Thiol-Reactive Cleavable Linkers.

7. Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water.

3. The effect of the intramolecular C-H⋯O interactions on the conformational preferences of bis-arylsulfones - 5-HT₆ receptor antagonists and beyond.