The reaction between an azide and triphenylphosphine (or phosphonite) to produce an iminophosphorane (the nucleophilic aza‐ylide) and subsequent hydrolysis to yield a primary amine is generally known as the Staudinger reaction.This reaction is a specific, high‐yielding reaction in which the iminophosphorane intermediate hydrolyzes spontaneously in the presence of water. Enantioselective Medium-Ring Lactone Synthesis through an NHC-Catalyzed Intramolecular Desymmetrization of Prochiral 1,3-Diols. Mechanisms of Staudinger Reactions within Density Functional Theory, Department of Chemistry, University of British Columbia, Vancouver BC V6T 1Z1, Canada. Heinz Heimgartner, Stephan P. Fritschi, Anthony Linden. We have proposed the origin of the stereoselectivity recently. Users are Д. В. Прохорова, Б.П. On New Staudinger Type Reactions of Phosphorus Centered Biradicaloids, [P(μ‐NR)] It also serves as an alternative way to navigate the website, and as a means of coming up with retrosynthetic ideas. the Altmetric Attention Score and how the score is calculated. Takahiko Ogawa, Tatsuya Suzuki, Nicholas M. Hein, Fraser S. Pick, Michael D. Fryzuk. Construction of Benzo-1,2,3-thiazaphosphole Heterocycles by Annulations of ortho-Phosphinoarenesulfonyl Fluorides with Trimethylsilyl Azide. azido complex with metallo-Staudinger reactivity. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. The reaction map is intended to provide insight into possible reactions one step before and after the title reaction. The regioselectivity of the Staudinger reaction with polyazides was investigated after the observation that the reduction of the tetrazide 23 with trimethylphosphine was regioselective. If you have previously obtained access with your personal account, please log in. Synthesis and Evaluation of 2-Deoxy-2-amino-β-cellobiosides as Cellulase Inhibitors. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Preparation and characterization of polymeric host molecules, β-cyclodextrin linked chitosan derivatives having different linkers. Low coordinate iron derivatives stabilized by a β-diketiminate mimic. DFT characterization of the mechanism for Staudinger/aza-Wittig tandem organocatalysis. Cyclo-Pnicta-triazanes: Biradicaloids or Zwitterions?. Alexander Hinz, Axel Schulz, Alexander Villinger, and Jan-Martin Wolter . Rebecca L. Melen, Alan J. Lough, Douglas W. Stephan. Staudinger ligation reaction scheme (azide-phosphine conjugation). Zeitschrift für anorganische und allgemeine Chemie. 2 The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting triphenylphosphine phenylimide, is then subjected to hydrolysis to produce a phosphine oxide and an amine: Recent progress on the stereoselective synthesis of cyclic quaternary α-amino acids. Fleet. Die Reaktion von Pentelidenkomplexen mit Carbodiimiden und Alkylaziden - ein direkter Weg zu viergliedrigen Heterocyclen. Four different initial reaction mechanisms have been found. Find more information about Crossref citation counts. Synthesis, structure, spectral, electrochemical and sensing properties of 3-amino boron-dipyrromethene and its derivatives. Synthesis, Structure–Activity Relationships, and Preclinical Evaluation of Heteroaromatic Amides and 1,3,4-Oxadiazole Derivatives as 5-HT4 Receptor Partial Agonists. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, By continuing to browse this site, you agree to its use of cookies as described in our, I have read and accept the Wiley Online Library Terms and Conditions of Use, Stabilization of acyclic phosphazides using the ortho-closo-dicarbadodecaboranyl residue. Journal of Chemical Theory and Computation. A stereoselective approach for the total synthesis of [2(S)-phenyl-propionyl]-2-piperidinone-3-(R)-yl-ester and its diastereomer. Comprehensive Organic Name Reactions and Reagents. This material is available free of charge via the Internet at Shane Rountree, Terry D. Butters, Raymond A. Dwek, George W.J. Synthesis and coordination chemistry of enamidophosphinimine scaffolds to generate diiron dinitrogen complexes. Use the link below to share a full-text version of this article with your friends and colleagues. International Journal of Chemical Kinetics. Theoretical Studies on the Adsorption of Si and C Chains onto Unfaulted and Faulted Si(111) Surfaces. Information about how to use the RightsLink permission system can be found at A metastable Ru 1) Kurti, L.; Czako, B.; Strategic Applications of Named Reactions in Organic Synthesis. Dangroo, A.A. Dar, R. Shankar, M.A. It also serves as an alternative way to navigate the website, and as a means of coming up with retrosynthetic ideas. Synthesis of novel peptides through Ugi-ligation and their anti-cancer activities. As there are a variety of methods for preparing azides readily, the Staudinger Reaction makes it possible to use -N 3 as an … Click on the reaction arrow to visit the page. Jia En Low, Joëlle Levalois-Grützmacher. The Staudinger reaction is an organic reaction used to convert an organic azide to a primary amine using a PR 3 compound (such as triphenylphosphine) and water. Jiliang Zhou, Levy L. Cao, Liu (Leo) Liu, Douglas W. Stephan. and (o-tolyl) Alkyl-guanidine Compounds as Potent Broad-Spectrum Antibacterial Agents: Chemical Library Extension and Biological Characterization. Devin H. A. Hiroaki Itoh, Kensuke Miura, Koichi Kamiya, Tomoya Yamashita, Masayuki Inoue. An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives. N.A. The effects of solvents, additives, and pathways of ketene generation on the stereoselectivity were investigated by using a clean Staudinger reaction, which is a sensitive reaction system to the stereoselectivity. The effects of substituents and solvent effects on the reaction mechanisms of the Staudinger reactions are discussed in detail. Jordi Burés, Manuel Martín, Fèlix Urpí and Jaume Vilarrasa. Cleavage of an aryl carbon–nitrogen bond of a phosphazido iron(