Abstract
This review provides a comprehensive survey of the literature on sulfenic acid chemistry from 1990 through June 2006, focusing the attention on salient aspects of their structures and involvement in organic processes. Even if the majority of known sulfenic acids cannot be isolated, some stable ones have been obtained, and their study helped dramatically the comprehension of chemical and physical properties of all sulfenic acids and indirectly of the role that Cys-SOHs play in protein biochemistry. Many papers have been published in the last fifteen years about the sulfenic acid intermediacy in organic chemistry. Once generated, they can be involved in intra- and intermolecular additions to unsaturated molecules. Few examples of sulfenic acid addition to double bonds have been recently described and most of them are intramolecular processes, whereas the addition of enantiopure sulfenic acids onto carbon-carbon triple bonds has been widely exploited in the synthesis of vinyl sulfoxides to be used in many stereoselective transformations. The thermic β- elimination from sulfinyl precursors is a way to generate sulfenic acids but it has been also used for removing the sulfinyl moiety from organic molecules and forming double bonds with controlled stereochemistry. Some significant applications of extrusion processes are also described in the present review.
Keywords: steric protecting group, X-ray crystallography, thermolysis, chiral bornyl group, D-mannopyranoses
Current Organic Chemistry
Title: Recent Advances and Perspectives in the Chemistry of Sulfenic Acids
Volume: 11 Issue: 12
Author(s): M.C. Aversa, A. Barattucci, P. Bonaccorsi and P. Giannetto
Affiliation:
Keywords: steric protecting group, X-ray crystallography, thermolysis, chiral bornyl group, D-mannopyranoses
Abstract: This review provides a comprehensive survey of the literature on sulfenic acid chemistry from 1990 through June 2006, focusing the attention on salient aspects of their structures and involvement in organic processes. Even if the majority of known sulfenic acids cannot be isolated, some stable ones have been obtained, and their study helped dramatically the comprehension of chemical and physical properties of all sulfenic acids and indirectly of the role that Cys-SOHs play in protein biochemistry. Many papers have been published in the last fifteen years about the sulfenic acid intermediacy in organic chemistry. Once generated, they can be involved in intra- and intermolecular additions to unsaturated molecules. Few examples of sulfenic acid addition to double bonds have been recently described and most of them are intramolecular processes, whereas the addition of enantiopure sulfenic acids onto carbon-carbon triple bonds has been widely exploited in the synthesis of vinyl sulfoxides to be used in many stereoselective transformations. The thermic β- elimination from sulfinyl precursors is a way to generate sulfenic acids but it has been also used for removing the sulfinyl moiety from organic molecules and forming double bonds with controlled stereochemistry. Some significant applications of extrusion processes are also described in the present review.
Export Options
About this article
Cite this article as:
M.C. Aversa , A. Barattucci , P. Bonaccorsi and P. Giannetto , Recent Advances and Perspectives in the Chemistry of Sulfenic Acids, Current Organic Chemistry 2007; 11 (12) . https://dx.doi.org/10.2174/138527207781369236
DOI https://dx.doi.org/10.2174/138527207781369236 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Some Implications of Receptor Kinase Signaling Pathway for Development of Multitargeted Kinase Inhibitors
Current Radiopharmaceuticals Cardiovascular Proteomics
Current Proteomics Novel Coronavirus Disease (COVID-19): A Narrative Review Based on Current Status
Anti-Infective Agents Protease Inhibitors as Promising Weapons against COVID-19: Focus on Repurposing of Drugs used to Treat HIV and HCV Infections
Current Topics in Medicinal Chemistry Fetal Alcohol Syndrome: A Cautionary Note
Current Pharmaceutical Design Recent Development and Future Perspective of Antitubercular Therapy
Anti-Infective Agents in Medicinal Chemistry Reactive Oxygen Species, Inflammation, and Lung Diseases
Current Pharmaceutical Design Benzenecarboxamide Analogs of Fluoroquinolones (BCFQs). Antibacterial Activity and SAR Studies
Letters in Drug Design & Discovery Nanocrystalline ZnO: A Competent and Reusable Catalyst for the Preparation of Pharmacology Relevant Heterocycles in the Aqueous Medium
Current Green Chemistry Structure-Activity Relationships of Glutamate Carboxypeptidase II (GCPII) Inhibitors
Current Medicinal Chemistry Bacterial Sepsis and Chemokines
Current Drug Targets The Interdisciplinary Management and Safety Perspectives in Endocrine, Metabolic and Psychiatric Disorder
Endocrine, Metabolic & Immune Disorders - Drug Targets Anti-Angiogenic Therapy: Strategies to Develop Potent VEGFR-2 Tyrosine Kinase Inhibitors and Future Prospect
Current Medicinal Chemistry Impact of Covid-19 on Mental Health: An Overview
Reviews on Recent Clinical Trials Virtual Screening Studies for Discovery of Novel Inhibitors of Inflammatory Process Targets
Current Pharmaceutical Design New Methodologies for Ligand-Based Virtual Screening
Current Pharmaceutical Design Homocysteine and Cerebral Stroke in Developing Countries
Current Medicinal Chemistry Design, Synthesis and Biopharmacological Profile Evaluation of New 2-((4- Chlorophenoxy)Methyl)-N-(Arylcarbamothioyl)Benzamides with Broad Spectrum Antifungal Activity
Current Organic Chemistry Inorganic Engineered Nanoparticles and Their Impact on the Immune Response
Current Drug Metabolism Synthesis and Biological Evaluation of Novel Bioisosteric Analogues of Dimebon™
Letters in Drug Design & Discovery