Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts
01 Oct 1967-Bulletin of the Chemical Society of Japan (The Chemical Society of Japan 公益社団法人 日本化学会)-Vol. 40, Iss: 10, pp 2380-2382
TL;DR: In this article, the reaction of carboxylic acid with triphenyl phosphine and diethyl azodicarboxylate in the presence of an alcohol has been studied.
Abstract: When n-valeric acid was treated with allyl diethyl phosphite and diethyl azodicarboxylate, allyl valeriate and diethyl N-(diethyl)phosphoryl hydrazodicarboxylate were obtained in good yields. Similarly ethyl benzoate was obtained in a nearly quantitative yield by the reaction of benzoic acid with triethyl phosphite and diethyl azodicarboxylate. The reaction of carboxylic acid with triphenyl phosphine and diethyl azodicarboxylate in the presence of an alcohol resulted in the formation of the corresponding esters of the carboxylic acid, triphenyl phosphine oxide, and diethyl hydrazodicarboxylate. The mechanisms of these reactions are also discussed.
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TL;DR: In this article, a reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds.
Abstract: The reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds. By the use of DEAD and TPP, diols and hydroxy acids gave cyclic ethers and lactones, respectively. The reaction of nucleosides with DEAD and TPP afforded triphenylphosphoranylnucleosides. Alcohols reacted with 2,6-di-t-butyl-4-nitrophenol in the presence of DEAD and TPP to give aci-nitroesters which converted into the corresponding carbonyl compounds.
3,209 citations
TL;DR: This review concludes that Etherification without Cyclization and N-Alkylation should be considered as separate science, and the proposed treatment of Etherification with Cyclization as a separate science should be reconsidered.
Abstract: 10. Patented Literature 2616 10.1. Esterification 2616 10.2. Ether Formation 2619 10.2.1. Etherification without Cyclization 2619 10.2.2. Etherification with Cyclization 2624 10.3. N-Alkylation 2625 10.4. Other Reactions 2627 11. Summary and Outlook 2628 12. Note Added in Proof 2628 13. Abbreviations Used in This Review 2629 14. Acknowledgments 2629 15. Supporting Information Available 2630 16. References 2630
909 citations
TL;DR: 1. Six-Membered Heterocycles with One Heteroatom 4155 7.6.1.
Abstract: 6.1. Oxadiazoles 4154 6.2. Diazaphospholes 4154 7. Six-Membered Heterocycles with One Heteroatom 4155 7.1. Pyridines 4155 7.2. Pyridinones 4155 7.3. Quinolines 4156 7.4. Quinolinones 4157 7.5. Isoquinolines 4157 7.6. Acridines 4158 7.7. Pyranones 4158 7.8. Flavones 4159 8. Six-Membered Heterocycles with Two Heteroatoms 4159 8.1. Pyridazinones 4159 8.2. Pyrimidines 4159 8.3. Pyrimidinones 4160 8.4. Quinazolines 4162 8.5. Quinazolinones 4162 8.6. Quinoxalines 4164 8.7. Quinoxalinediones 4165 8.8. Oxazines 4165 8.9. Oxazinones 4166 8.10. Thiazines 4166 9. Six-Membered Heterocycles with Three Heteroatoms 4166
549 citations
TL;DR: In this paper, the authors summarized the results reported mainly within the last 10 years, and it is quite clear from the growing number of emerging publications in this field that the possibility to utilize multicomponent technology allows reaction conditions to be accessed that are very valuable for organic synthesis.
Abstract: Multicomponent reactions have gained significant importance as a tool for the synthesis of a wide variety of useful compounds, including pharmaceuticals. In this context, the multiple component approach is especially appealing in view of the fact that products are formed in a single step, and the diversity can be readily achieved simply by varying the reacting components. The eco-friendly, solvent-free multicomponent approach opens up numerous possibilities for conducting rapid organic synthesis and functional group transformations more efficiently. Additionally, there are distinct advantages of these solvent-free protocols since they provide reduction or elimination of solvents thereby preventing pollution in organic synthesis “at source”. The chemo-, regio- or stereoselective synthesis of high-value chemical entities and parallel synthesis to generate a library of small molecules will add to the growth of multicomponent solvent-free reactions in the near future. In this review we summarized the results reported mainly within the last 10 years. It is quite clear from the growing number of emerging publications in this field that the possibility to utilize multicomponent technology allows reaction conditions to be accessed that are very valuable for organic synthesis. Therefore, diversity oriented synthesis (DOS) is rapidly becoming one of the paradigms in the process of modern drug discovery. This has spurred research in those fields of chemical investigation that lead to the rapid assembly of not only molecular diversity, but also molecular complexity. As a consequence multi-component as well as domino or related reactions are witnessing a new spring.
420 citations
TL;DR: A review of progress in the MITSUNOBU this article reaction can be found in this article, with a focus on the MIT SUNOBU reaction and a review of the progress.
373 citations
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TL;DR: In this paper, a trivalent phosphorus compound was oxidized by means of diethyl azodicarboxylate and either benzyl or allyl alcohol to give the corresponding phosphine oxide or trialkyl phosphates.
Abstract: Trivalent phosphorus compounds, phosphine or trialkylphosphites, have been oxidized by means of diethyl azodicarboxylate and either benzyl or allyl alcohol to give the corresponding phosphine oxide or trialkyl phosphates. The reaction was then extended to the phosphorylation of alcohols. When allyl diethyl phosphite was treated with diethyl azodicarboxylate in the presence of an alcohol at room temperature, a corresponding alkyl diethyl phosphate and diethyl N-allyl hydrazodicarboxylate were obtained in good yields. On the other hand, when phenol was treated with allyl diethyl phosphite and diethyl azodicarboxylate, diethyl phenyl phosphate, allyl phenyl ether and diethyl hydrazodicarboxylate were obtained. The mechanism of their formation will also be discussed.
257 citations
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