With its coverage of organic name reactions and reagents, Comprehensive Organic Name Reactions and Reagents is the largest, most. Comprehensive Organic Name Reactions and Reagents. Author(s): Stork Reaction · Abstract · Full text · PDF Tscherniac‐Einhorn Reaction. Request PDF on ResearchGate | On Mar 1, , Siegfried R. Waldvogel and others published Comprehensive Organic Name Reactions and.
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Book Review of Comprehensive Organic Name Reactions and Reagents Abstract: This chapter presents style conventions for citing references within a manuscript and for listing complete reference citations. Many of Abstract | Hi- Res PDF. Comprehensive organic name reactions and reagents [electronic resource]. Responsibility: Zerong Wang. Imprint: Hoboken, N.J.: John Wiley, c Physical. "This three-volume compendium of organic name reactions and reagents is one of the most comprehensive and complete works to concisely, yet fully, cover the.
Chemical reactions. Chemical tests and reagents. More Details author. Wang, Zerong Daniel Zerong. Appeared in Choice on The synthetic organic chemistry literature requires a sophisticated indexing scheme to organize and consolidate information, and as such, the use of multivolume works to compile references has been a traditional approach in the discipline.
Therefore, it is puzzling why Wiley pursued this new three-volume compendium. The editing and production quality of the proposed mechanisms and experimental examples is acceptable, but errors exist in this edition for example, see the chapter titled "Abnormal Claisen Rearrangement" for inadvertent carbon chain homologation. The author's effort to create this work is commendable, but Wang Univ.
One problem associated with this index includes the idiosyncratic authentication of a unique reaction name. Further, readers need extensive training in name reactions and chemical transformations at the upper-graduate level to understand how this index works.
Wang tries to ameliorate this problem by supplying a "Reaction Type Summary" in an appendix. Reaction wheels and lists of related reactions are helpful, but only about of the reactions are actually correlated.
This work is valuable from an archival viewpoint, but for current active research, it does not represent a significant advancement. Summing Up: With reservations.
Researchers and faculty. Slough Kalamazoo College. This book set will be valuable to any laboratory pursuing synthetic organic chemistry and as a comprehensive resource to chemists involved in the synthesis of organic compounds.
Over name reactions with over 36 citations are presented in a very clear, organized, and easy to navigate manner.
The presentation and discussion of each name reaction consist of eight subsections; a general description and discussion of the reaction are followed by a representative reaction scheme that uses substructures to show the chemical transformation. A section is also devoted to showing a relatively detailed proposed mechanism for each reaction, as appropriate. Reported modifications to the reaction, application s of the reaction, and related types of reactions are then discussed.
One or more additional cited experimental examples are also presented, followed by a comprehensive list of references. This set of books is complemented by a number of useful appendices. Appendix 1 is a schematic reaction index, providing a straightforward visual summary of each reaction. Appendix 2 summarizes the reactions by transformation type e. Appendix 3 is an interesting summary of citations for the initial publication of each name reaction and reagent.
Appendices 4 and 5 cover journal abbreviations and additional citation statistics and summaries. The subject index is extensive, and the list of chemical abbreviations for reagents is complemented with the structure of each. One surprise with this series is that a few reactions are classified as name reactions based on the lab that originally used or published the specific reaction, even though the reaction is or has not otherwise been generally considered a name reaction.
However, this expansion is perhaps less of a negative and more of a manifestation of just how comprehensive these volumes are in coverage of name reactions and reagents. To find out how to look for other reviews, please see our guides to finding book reviews in the Sciences or Social Sciences and Humanities. Bowker Data Service Summary. This is a comprehensive resource for students and bench chemists navigating the ever-growing group of named reactions and reagents.
It contains detailed reaction schemes and mechanism illustrations for each listing and includes information on the application of each named reaction.
The most comprehensive collection of name reactions and reagents available today for students and bench chemists navigating the ever-growing group of named reactions and reagents, "Comprehensive Organic Name Reactions and Reagents: With this idea in mind, we embarked on the development of a strategy to achieve the olefination of carbonyls. Typical classifications of olefination methodologies tend to discriminate between the nature of the reagent employed, such as phosphonium ylides Wittig , sulfones Julia , silicon-stabilized carbanions Peterson , or metal alkylidenes Tebbe.
Given that all these reactions are assumed to proceed through cyclic intermediates which undergo different types of cycloreversion reactions in the olefin-yielding step, we propose a different and perhaps richer view, assigning a classification based on the ring size of that key reaction intermediate Fig.
For instance, the modified Julia so-called Julia—Kocienski reaction involves a five-membered spirocyclic intermediate, whereas the Wittig, Tebbe, and Peterson olefinations all proceed via a four-membered ring, as does recently developed aza-phosphetanes chemistry 15 , The conspicuous scarcity of three-membered ring intermediates in this analysis drove us to develop a new approach to olefination relying on an aziridine intermediate 17 , 18 , 19 , In this context, we herein present an unusual and conceptually method for the synthesis of olefins from aldehydes, which we believe brings further diversity to the field while possessing synthetic advantages in its own right.
Results Initial considerations Our approach, depicted in Fig. We proposed the transient generation of an N-iminyl aziridine and its subsequent cheletropic cycloreversion 23 , 24 , 25 , 26 , 27 , 28 to unveil the desired olefin product. At the outset of the project, we foresaw two main challenges.
First, the formation of an N-iminyl aziridine from a carbonyl precursor in a synthetically useful manner 29 , 30 and then finding appropriate conditions for a facile cheletropic elimination We eventually settled for the aziridination of an in-situ generated N-iminyl imine azine as route to the three-membered ring intermediate Fig. Key to addressing the two aforementioned challenges would be the nature of the hydrazone R1 and R2 substituents.
First experiments In initial experiments, we sought to convert 2-napthaldehyde as model substrate to the corresponding azine. A facile condensation between the two delivered the crude azine 2a in analytically pure form, on which we explored suitable conditions for aziridine formation. We next turned our attention to the use of sulfur ylides, generated in situ from sulfonium salts, as nucleophiles Encouraged by this result we turned to sulfoxonium ylides, known to exhibit greater stability, which allowed us to increase the temperature of the reaction Table 1 Optimization of reaction conditions Full size table Substrate scope With suitable conditions for this olefination in hand, we next explored the scope of aromatic aldehydes.
As shown in Fig. Due to the mildness of the reaction conditions, a wide range of functional groups are well tolerated: esters, nitro groups, amides, ethers, and aryl halides.
Importantly, although the overall transformation implies one extra step for N-iminyl imine preparation, this is a very facile operation for all aldehydes studied. Indeed, simple stirring at room temperature in presence of MgSO4 leads to quantitative conversion into the free-flowing, generally yellow powder products.
The only side products, detected in the crude products mixtures, are the homologated azines. Yields were calculated on isolated yield over two steps. Surprisingly, the reaction of sulfoxonium ylides with unsaturated azines resulted in a clean 1,2-addition to generate dienes 4 after cheletropic elimination.
This effectively allows a smooth access to synthetically useful E-configured di- and trisubstituted dienes 4a—4d. Yields calculated on isolated material over two synthetic steps, r. In this case, the use of hydrazone 1b was crucial, as when 1a was employed, a rapid isomerization to an unstable side product tentatively assigned as the N-iminyl enamine tautomer was observed.
Other types of highly conjugated hydrazones with more electron rich system 1d or more electron poor system 1e , were tested but failed in providing the desired product. Compound 1e exhibited prohibitively slow rate of azine formation and provided trace amounts of olefin with considerable degradation.
Compound 1d led to efficient azine formation, but nucleophilic attack from the sulfoxonium ylide was not observed. Finally with the use of hydrazone 1b, the desired olefins could be isolated in good yields after cheletropic extrusion triggered by heating in toluene 5a, 5b.
Moreover, the reaction conditions tolerate standard protecting groups such as silyl ether- 5c and benzyl 5d. To test the limit of applicability of this olefination procedure Fig.
Finally, we investigated the applicability of the methodology to the formation of disubstituted olefins Fig. By employing appropriately substituted and readily accessible sulfoxonium salts, we were able to obtain internal olefins in good to high yields, starting from aromatic aldehydes 7a, 7b, 7c or aliphatic and conjugated aldehydes 7d, 7e. Notably, the alkene products were obtained with marked E selectivity. This might be a consequence of either stereospecific cheletropic elimination from the more stable trans-aziridine intermediate or non-concerted ring-opening pathways that allow isomerization to take place 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , This E-selectivity is a noteworthy trait of the method.
Yields are calculated on isolated material over two synthetic steps. It should be noted that, in contrast to Wittig procedures, which usually lead to a significant erosion of enantiopurity by base-mediated epimerization 35 , the procedure reported herein produced the desired olefin 7 with minimal loss of chiral information.
Yields are calculated on isolated material over two synthetic steps Full size image Mechanistic experiments Finally, we performed control experiments to propose a reasonable mechanism.