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Introduction to the organic nomenclature system
According to the International Union of Pure & Applied Chemistry (IUPAC), the organic chemistry nomenclature is a technique for naming organic chemical compounds in chemical nomenclature. It is presented in the Organic Chemistry Nomenclature (OCN). Guidelines for systematic nomenclature of organic compounds developed by the International Union of Pure & Applied Chemistry and frequently updated. The stem name, prefix, and suffix are the three main components of the IUPAC nomenclature for organic compounds. It is highlighted in this volume that the use of alternative names to draw attention to structural characteristics shared by a number of compounds, or to take into account a particular context does not preclude the use of preferred IUPAC names. The \"preferred IUPAC nomenclature\" includes the names that are chosen by the institution. In the context of \"general IUPAC nomenclature, \" any name other than a preferred IUPAC name is acceptable as a standard IUPAC name as long as it is unambiguous and adheres to the principles of the IUPAC recommendations herein.
eBook
Computational planning of the synthesis of complex natural products
Training algorithms to computationally plan multistep organic syntheses has been a challenge for more than 50 years
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. However, the field has progressed greatly since the development of early programs such as LHASA
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, for which reaction choices at each step were made by human operators. Multiple software platforms
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are now capable of completely autonomous planning. But these programs ‘think’ only one step at a time and have so far been limited to relatively simple targets, the syntheses of which could arguably be designed by human chemists within minutes, without the help of a computer. Furthermore, no algorithm has yet been able to design plausible routes to complex natural products, for which much more far-sighted, multistep planning is necessary
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and closely related literature precedents cannot be relied on. Here we demonstrate that such computational synthesis planning is possible, provided that the program’s knowledge of organic chemistry and data-based artificial intelligence routines are augmented with causal relationships
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, allowing it to ‘strategize’ over multiple synthetic steps. Using a Turing-like test administered to synthesis experts, we show that the routes designed by such a program are largely indistinguishable from those designed by humans. We also successfully validated three computer-designed syntheses of natural products in the laboratory. Taken together, these results indicate that expert-level automated synthetic planning is feasible, pending continued improvements to the reaction knowledge base and further code optimization.
A synthetic route-planning algorithm, augmented with causal relationships that allow it to strategize over multiple steps, can design complex natural-product syntheses that are indistinguishable from those designed by human experts.
Journal Article
Organic chemistry I for dummies
\"Clear explanations of organic chemistry principles; logical approaches to solving organic chemistry problems; tips to help you ace your Organic Chemistry I course\"--Cover.
Book
Superelectrophiles and their chemistry
Superelectrophiles and Their Chemistry contains, for the first-time, a discussion of the basics of this emerging field of organic chemistry, alongside tools to help the reader apply the chemistry. Specific tools include an evaluation of the ways to increase the strength of electrophiles, the classification of superelectrophiles, the solvation issues, a review of methods for studying superelectrophilicity, with details of the superelectrophiles that have been identified and studied. Additional information includes substituent effects in activation of superelectrophiles, and solvation in chemical reactions, as well as an insightful look into future applications.
eBook
Flux synthesis of two-dimensional covalent organic frameworks
Covalent organic frameworks (COFs) are crystalline porous polymers constructed from organic building blocks into ordered two- or three-dimensional networks through dynamic covalent bonds. Attributed to their high porosity, well-defined structure, tailored functionality and excellent chemical stability, COFs have been considered ideal sorbents for various separation applications. The synthesis of COFs mainly employs the solvothermal method, which usually requires organic solvents in sealed Pyrex tubes, resulting in unscalable powdery products and environmental pollution that seriously limits their practical applications. Herein, our protocol focuses on an emerging synthesis method for COFs based on organic flux synthesis without adding solvents. The generality of this synthesis protocol has been applied in preparing various types of COFs, including olefin-linked, imide-linked, Schiff-based COFs on both gram and kilogram scales. Furthermore, organic flux synthesis avoids the disadvantages of solvothermal synthesis and enhances the crystallization and porosity of COFs. Typically, COF synthesis takes 3–5 d to complete, and subsequent washing procedures leading to pure COFs need 1 d. The procedure for kilogram-scale production of COFs with commercially available monomers is also provided. The resulting COFs are suitable for separation applications, particularly as adsorbent materials for industrial gas separation and water treatment applications. The protocol is suited for users with prior expertise in the synthesis of inorganic materials and porous organic materials.
Key points
This protocol describes a flux synthesis approach for two-dimensional covalent organic frameworks (COFs).
Compared with other approaches, the method described here does not use solvents, making it environmentally friendly, and is scalable up to the kilogram scale. In addition, high-quality COF monoliths can be generated rather than powdery products, and COFs prepared by this protocol usually possess higher crystallinity and BET surface area than those prepared by traditional solvothermal methods.
This protocol describes a flux synthesis approach for two-dimensional covalent organic frameworks. Compared with other approaches, this method does not use solvents, making it environmentally friendly, and is scalable up to the kilogram scale.
Journal Article
Methods and applications of cycloaddition reactions in organic syntheses
Advanced tools for developing new functional materials and applications in chemical research, pharmaceuticals, and materials science
Cycloadditions are among the most useful tools for organic chemists, enabling them to build carbocyclic and heterocyclic structures. These structures can then be used to develop a broad range of functional materials, including pharmaceuticals, agrochemicals, dyes, and optics. With contributions from an international team of leading experts and pioneers in cycloaddition chemistry, this book brings together and reviews recent advances, trends, and emerging research in the field.
Methods and Applications of Cycloaddition Reactions in Organic Syntheses focuses on two component cycloadditions, with chapters covering such topics as:
* N1 unit transfer reaction to C–C double bonds
* [3+2] Cycloaddition of ?, ?-unsaturated metal-carbene complexes
* Formal [3+3] cycloaddition approach to natural product synthesis
* Development of new methods for the construction of heterocycles based on cycloaddition reaction of 1,3-dipoles
* Cycloreversion approach for preparation of large ?-conjugated compounds
* Transition metal-catalyzed or mediated [5+1] cycloadditions
Readers will learn methods for seamlessly executing important reactions such as Diels-Alder and stereoselective dipolar reactions in order to fabricate heterocyclic compounds, natural products, and functional molecules. The book not only features cutting-edge topics, but also important background information, such as the contributors' process for developing new methodologies, to help novices become fully adept in the field. References at the end of each chapter lead to original research papers and reviews for facilitating further investigation of individual topics.
Covering the state of the science and technology, Methods and Applications of Cycloaddition Reactions in Organic Syntheses enables synthetic organic chemists to advance their research and develop new functional materials and applications in chemical research, pharmaceuticals, and materials science.
eBook