Lithium Aluminum Hydride–Chromium(III) Chloride
作者： Timothy A. Gillespy
关键词:
摘要: (LiAlH4) [16853-85-3] AlH4Li (MW 37.96) InChI = 1S/Al.Li.4H/q-1;+1;;;; InChIKey = OCZDCIYGECBNKL-UHFFFAOYSA-N (CrCl3) [10025-73-7] Cl3Cr (MW 158.35) InChI = 1S/3ClH.Cr/h3*1H;/q;;;+3/p-3 InChIKey = QSWDMMVNRMROPK-UHFFFAOYSA-K (reducing agent for reductive dimerization of allylic halides,2 halide reduction,2, 3 and alkylation carbonyls2, 4, 5) Physical Data: see Lithium Aluminum Hydride. Solubility: sol THF, DMF, HMPA. Form Supplied in: prepared in situ from commercially available compounds. Preparative Method: by adding lithium aluminum hydride to anhydrous chromium(III) chloride suspended THF at 0 °C under an argon atmosphere. A small amount zinc metal helps solubilize the chloride. 2:1 molar ratio yields most effective reagent.2 Handling, Storage, Precautions: see Hydride. Bottles hydride–chromium(III) reagent should be refrigerated stored argon.
sci-hub.se 参考文章(12)
Susumi Hatakeyama, Hirotoshi Numata, Ken Osanai, Seiichi Takano, Efficient enantiospecific synthesis of key A-ring synthons for the preparation of 1.alpha.,25-dihydroxyvitamin D3 using a chromium(II)-mediated reaction Journal of Organic Chemistry. ,vol. 54, pp. 3515- 3517 ,(1989) , 10.1021/JO00276A003
Kazuhiko Takai, Tooru Kuroda, Shigeki Nakatsukasa, Koichiro Oshima, Hitosi Nozakil, Aldehyde-selective addition of alkynylchromium compounds prepared by reduction of alkynyl halides with chromium(II) reagent Tetrahedron Letters. ,vol. 26, pp. 5585- 5588 ,(1985) , 10.1016/S0040-4039(01)80894-7
Yoshitaka Okude, Tamejiro Hiyama, Hitosi Nozaki, Reduction of organic halides by means of CrCl3-LiAlH4 reagent in anhydrous media Tetrahedron Letters. ,vol. 18, pp. 3829- 3830 ,(1977) , 10.1016/S0040-4039(01)83365-7
Johann Mulzer, Lars Kattner, Achim R. Strecker, Christian Schroeder, Juergen Buschmann, Christian Lehmann, Peter Luger, Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer Journal of the American Chemical Society. ,vol. 113, pp. 4218- 4229 ,(1991) , 10.1021/JA00011A025
P. Auvray, P. Knochel, J.F. Normant, Diastereoselective addition of the 2-phenylsulfonyl-substituted allylic bromides to aldehydes in the presence of zinc or chromium (II) chloride Tetrahedron Letters. ,vol. 27, pp. 5091- 5094 ,(1986) , 10.1016/S0040-4039(00)85141-2
Yoshitaka Okude, Shigeo Hirano, Tamejiro Hiyama, Hitosi Nozaki, Grignard-type carbonyl addition of allyl halides by means of chromous salt. A chemospecific synthesis of homoallyl alcohols Journal of the American Chemical Society. ,vol. 99, pp. 3179- 3181 ,(1977) , 10.1021/JA00451A061
Hiroto Nagaoka, Yoshito Kishi, Further synthetic studies on rifamycin s Tetrahedron. ,vol. 37, pp. 3873- 3888 ,(1981) , 10.1016/S0040-4020(01)93261-2
Charles T. Buse, Clayton H. Heathcock, Acyclic stereoselection. III. Synthesis of threo-3-hydroxy-2-methylcarboxylic acids☆ Tetrahedron Letters. ,vol. 19, pp. 1685- 1688 ,(1978) , 10.1016/S0040-4039(01)94640-4
Pierre Place, Françoise Delbecq, Jacques Gore, Utilisation d'un derive organique du chrome dans la synthese de composes alleniques Tetrahedron Letters. ,vol. 19, pp. 3801- 3802 ,(1978) , 10.1016/S0040-4039(01)95062-2
Nobuo Kato, Shinya Tanaka, Hitoshi Takeshita, Total Synthesis of Cycloaraneosene, a Fundamental Hydrocarbon of “epi”-Fusicoccane Diterpenoids, and the Structure Revision of Its Congener, Hydroxycycloaraneosene Chemistry Letters. ,vol. 15, pp. 1989- 1992 ,(1986) , 10.1246/CL.1986.1989