• Nitrene addition to alkenes is a well-established method for the synthesis of aziridines. (wikipedia.org)
  • The Hoch-Campbell ethylenimine synthesis involves the reaction of certain oximes with Grignard reagents, which affords aziridines. (wikipedia.org)
  • The De Kimpe aziridine synthesis allows for the generation of aziridines by reacting an α-chloroimine with a nucleophile, such as hydride, cyanide, or a Grignard reagent. (wikipedia.org)
  • Aziridines are commonly used in synthesis for chemical bond expansions and functional group transformations. (moltuslab.com)
  • The chemistry of epoxides and Aziridines or any other three-membered ring heterocycles, has caught the attention of synthetic chemists for more than a century, owing to the essentially high reactivity of these small-ring heterocycles. (moltuslab.com)
  • Morandi, B. Atom-Economical Cobalt-Catalysed Regioselective Coupling of Epoxides and Aziridines with Alkenes. (mpg.de)
  • This chapter provides an overview of the methods by which epoxides and aziridines can be prepared via nucleophilic attack at the C. O or C. N bond. (hud.ac.uk)
  • PolyAziridine Global pledges to address this by offering not just a complete line of polyfunctional aziridine cross-linkers but also to provide the technical support so important to their successful use. (polyaziridineglobal.com)
  • The request noted concerns about workers' exposure to a new, two-component, water-based polyurethane paint (water-based polyurethane paint with polytetrafluoroethylene and a polyfunctional aziridine cross-linker) that is applied to automotive/truck rubber seals (vehicle sealing) on the dual durometer (DD) extrusion lines. (cdc.gov)
  • Several routes have been developed for the syntheses of aziridines (aziridination). (wikipedia.org)
  • The parent compound is aziridine (or ethylene imine), with molecular formula C 2H 4NH. (wikipedia.org)
  • The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. (wikipedia.org)
  • Aziridine is the nitrogen analog of ethylene oxide, and it needs to be protected with tosyl, or the grignard will be quenched. (thevespiary.org)
  • The recent research and development of Aziridine chemistry has followed two main paths. (moltuslab.com)
  • Aziridines are reactive substrates in ring-opening reactions with many nucleophiles due to their ring strain. (wikipedia.org)
  • Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. (wikipedia.org)
  • Angle strain in aziridine also increases the barrier to nitrogen inversion. (wikipedia.org)
  • Thermolysis or photolysis of triazolines expels nitrogen, producing an aziridine. (wikipedia.org)
  • Aziridines are saturated three-membered ring compounds, that contain two carbons and one nitrogen atom. (moltuslab.com)
  • An amine functional group displaces the adjacent halide in an intramolecular nucleophilic substitution reaction to generate an aziridine. (wikipedia.org)
  • 50] "Nucleophilic Rh I Catalyzed Selective Isomerization of Terminal Aziridines to Enamides", Y. Tian, D. Kunz*, ChemCatChem 2020 , 12 , 4272-4275. (uni-tuebingen.de)
  • Although the aziridine motif appears in some natural products, interest in these models comes from the easy access to amine-protected derivatives obtained via the nucleophilic ring-opening of aziridines. (umontreal.ca)
  • Nucleophilic ring-opening of aziridines has been thoroughly studied for a variety of nucleophiles and aziridines. (umontreal.ca)
  • Or, même si le motif aziridine se retrouve dans certains produits naturels, l'intérêt de sa synthèse provient en partie de l'accès facile à différents composés contenant une fonction amine protégée qui peuvent être obtenus suite à l'ouverture d'aziridines par différents nucléophiles. (umontreal.ca)
  • We have developed a highly stereospecific cyclization of aziridine silanols into 1′-amino-tetrahydrofurans. (ku.edu)
  • A novel rearrangement of 2-vinyl aziridine 2-carboxylates to unusual chiral cyclic sulfoximines is described herein. (nottingham.ac.uk)
  • The existing and state-of-the-art features catalytic, highly enantioselective aziridinations, reliable ring-opening transformations, and stereoselective cycloadditions, all of which illustrate the unique reactivity of Aziridines. (moltuslab.com)
  • As electrophiles, aziridines are subject to attack and ring-opening by endogenous nucleophiles such as nitrogenous bases in DNA base pairs, resulting in potential mutagenicity. (wikipedia.org)
  • Alkene + DPH → R h 2 ( C O 2 R ) 4 {\displaystyle {\xrightarrow {Rh_{2}(CO_{2}R)_{4}}}} Aziridine For instance, Ph-Aziridine-Me can be synthesized by this method and then converted by ring opening reaction to (D)-amphetamine and (L)-amphetamine (the two active ingredients in Adderall). (wikipedia.org)
  • The novel ring-opening reaction of enantiopure N-activated aziridines 1 with anions 2 derived from 1,3-dithiane proceeds regiospecifically at the carbon of lesser substitution. (lancs.ac.uk)
  • Yields for the closest analog I could find to this aziridine reaction are around 60%, couldn't find any actual *quantitative* data on reaction rates though. (thevespiary.org)
  • N-Diphenylphosphinyl-3-ethenyl-2-phenylaziridine (1) and N-diphenylphosphinyl-3-ethenyl-2-(4-bromophenyl)aziridine (2) are prepared by reaction of α-bromo allyllithium with N-diphenylphosphinyl aldimines in the presence of zinc chloride. (hud.ac.uk)
  • Ring opening of aziridines with pendant silanols is compatible with a range of substrates. (ku.edu)
  • Aziridine is a highly reactive and volatile chemical. (moltuslab.com)
  • The International Agency for Research on Cancer (IARC) classifies aziridine compounds as possibly carcinogenic to humans (IARC Group 2B). (wikipedia.org)
  • Aldimines (generated in situ from aldehydes and amines) react readily with ethyl diazoacetate in the presence of 2 mol% of Bi(OTf) 3 in [bmim]PF 6 to produce the corresponding aryl aziridine carboxylates in high yields with excellent cis -diastereoselectivity. (organic-chemistry.org)
  • Any number of Cu-based catalysts are highly effective, with many giving QUANTITATIVE yields of the aziridine product. (thevespiary.org)
  • This entry was posted on March, 06, 2020 at 10 : 19 am and is filed under Aziridine . (moltuslab.com)
  • PolyAziridine Global is dedicated to the aziridine crosslinker market and to be the repository of this technology. (polyaziridineglobal.com)
  • Polyfunctional aziridines are very versatile molecules with wide-ranging usage in coatings and adhesive applications. (polyaziridineglobal.com)
  • Aziridine is a monomer that finds use in the preparation of cationic polymers. (moltuslab.com)
  • Second, appropriate control over the subsequent ring-opening transformations of aziridines. (moltuslab.com)
  • Organocatalytic Ring-opening Polymerization Towards Poly(cyclopropane)s, Poly(lactame)s, Poly(aziridine)s, Poly(siloxane)s, Poly(carbosiloxane)s, Poly(phosphate)s, Poly(phosphonate)s, Poly(thiolactone)s, Poly(thionolactone)s and Poly(thiirane)s. (mpg.de)
  • These conditions were also used in the ring-opening of various PhTroc-protected aziridines and the results are disclosed herein. (umontreal.ca)
  • Palladium Pincer Complex Catalyzed Substitution of Vinyl Cyclopropanes, Vinyl Aziridines, and Allyl Acetates with Tetrahydroxydiboron. (organic-chemistry.org)
  • Aziridine is a clear and colorless oily liquid substance that has a strong odor of ammonia. (moltuslab.com)
  • Even if the Aziridine is a gas one could dissolve the Aziridine in an inert liquid. (thevespiary.org)