Shriver and Atkins. − 0000004705 00000 n Part I", Angewandte Chemie International Edition in English, "An efficient synthesis of γ-imino- and γ-amino-β-enamino esters", https://www.organic-chemistry.org/synthesis/N1H/reductionsazides.shtm, Synthesizing, Purifying, and Handling Organic Azides, https://en.wikipedia.org/w/index.php?title=Azide&oldid=986290689, Pages that use a deprecated format of the chem tags, Creative Commons Attribution-ShareAlike License, Some organic and other covalent azides are classified as highly explosive and toxic: inorganic azides as neurotoxins; azide ions as. [17], Sodium azide is the propellant in automobile airbags. The dominant application of azides is as a propellant in air bags. Organic azides engage in useful organic reactions. 0000003998 00000 n Die thermische Zersetzung erfolgt bei höheren Temperaturen in drei Schritten. It reacts with epoxides, causing a ring-opening; it undergoes Michael-like conjugate addition to 1,4-unsaturated carbonyl compounds.[1]. Vol. Jeon, P. J. Walsh, W. A. Nugent: M. T. Reetz, M. W. Drewes, R. Schwickardi: T. N. Dymova, D. P. Aleksandrov, V. N. Konopolev, T. A. Silina, AS Sizareva: In: Entsorgung von Lithiumaluminiumhydridabfällen, Chiral Media for Asymmetric Solvent Inductions. They react with amines to give the corresponding azides: A classic method for the synthesis of azides is the Dutt–Wormall reaction[8] in which a diazonium salt reacts with a sulfonamide first to a diazoaminosulfinate and then on hydrolysis the azide and a sulfinic acid. 0000023560 00000 n x�b``�``�d`g`�J`a@ �;���ffi��^0\�����0y%ê�F��!O��rb ;-���7���qQŹ���&�W�����������9cU�P���3��m��\=��w���Y6�ferT� 0000122733 00000 n 0000077128 00000 n 0000056003 00000 n 0000042550 00000 n Novel ring contractions induced by lah reduction of addition products of iodine azide to alkyl substituted cyclobutenes Author links open overlay panel Michael J. O'Hare Daniel Swern Show more N 0000072293 00000 n Novel ring contractions induced by lah reduction of addition products of iodine azide to alkyl substituted cyclobutenes. H. Sajiki, Tetrahedron Lett. 0000125530 00000 n 0000024076 00000 n 0000123061 00000 n Often as a solution in diethyl ether and followed by an acid workup, it will convert esters, carboxylic acids, acyl chlorides, aldehydes, and ketones into the corresponding alcohols (see: carbonyl reduction). 290 0 obj <>stream 0000022796 00000 n 0000059663 00000 n 0000038045 00000 n We use cookies to help provide and enhance our service and tailor content and ads. {\displaystyle {\ce {^{-}N={\overset {+}{N}}=N^{-}}}} xref 0000014063 00000 n 0000039157 00000 n [11], Many inorganic covalent azides (e.g., chlorine, bromine, and iodine azides) have been described. They decompose with sodium nitrite when acidified. Azides may be converted to amines by hydrogenation, but another possibility is the Staudinger Reaction, which is a very mild azide reduction. 0000123508 00000 n 0000104596 00000 n [7] Nach Abfiltrieren des Lithiumchlorids und Entfernen des Ethers bleibt Lithiumaluminiumhydrid zurück. As a pseudohalogen compound, sodium azide generally displaces an appropriate leaving group (e.g., Br, I, OTs) to give the azido compound. 0000124467 00000 n It is more powerful than the related reagent sodium borohydride owing to the weaker Al-H bond compared to the B-H bond. Lithiumaluminiumhydrid ist ein starkes Reduktionsmittel der organisch-synthetischen Chemie und reduziert selektiv fast alle Kohlenstoff-Heteroatom-Doppel- und -Dreifachbindungen wie beispielsweise Carbonyle oder Nitrile, es schont dagegen C=C-Doppelbindungen und C≡C-Dreifachbindungen (Alkene/Alkine), es sei denn, diese sind konjugiert zu bestimmten aktivierenden Gruppen; so wird z.
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