Subscribe to RSS
DOI: 10.1055/s-0030-1259002
1,3-Dichloroacetone
Publication History
Publication Date:
22 October 2010 (online)
Introduction
1,3-Dichloroacetone (CAS: 534-07-6) is the simplest and most common example of the α,α′-dihaloketone derivatives. It is a crystalline solid (mp 39-41 ˚C), corrosive, toxic, and has to be handled in a fume hood. It shows a good solubility in organic solvents and a very high high chemical reactivity, justified by the presence of three vicinal electrophilic carbons, which enables it to undergo several chemical transformations. Although it is commercially supplied, it may be prepared by chlorination of acetone in methanol as proposed by Gallucci. [¹] Alternatively, an expeditious synthesis has been reported by Barluenga via the in situ formation of a lithium carbenoid, such as chloromethyllithium, which reacts with the ethyl ester of the chloroacetic acid, as shown in Scheme [¹] . [²]
Scheme 1
- 1
Gallucci RR.Going R. J. Org. Chem. 1981, 46: 2532 - 2
Barluenga J.Llavona L.Concellon JM.Yus M. J. Chem. Soc., Perkin Trans. 1 1991, 297 - 3
Taillier C.Hameury T.Bellosta V.Cossy J. Tetrahedron 2007, 63: 4472 - 4
Alonso D.Caballero E.Medarde M.Tomé F. Tetrahedron Lett. 2007, 48: 907 - 5
Caselli E.Tosi G.Forni A.Bucciarelli M.Prati F.
Il Farmaco 2003, 58: 1029 - 6
Bergeot O.Corsi C.Qacemi ME.Zard SZ. Org. Biomol. Chem. 2006, 4: 278 - 7
de Greef M.Zard SZ. Org. Lett. 2007, 9: 1773 - 8
Lukowska E.Plenkiewicz J. Tetrahedron: Asymmetry 2007, 18: 1202 - 9
Hjelmgaard T.Givskov M.Nielsen J. Org. Biomol. Chem. 2007, 5: 344 - 10
Li B.Lyle MPA.Chen G.Li J.Hu K.Tang L.Alaoui-Jamali MA.Webster J. Biorg. Med. Chem. 2007, 15: 4601 - 11
Bakunova SM.Bakunov SA.Wenzler T.Barszcz T.Werbovetz KA.Brun R.Hall JE.Tidwell RR.
J. Med. Chem. 2007, 50: 5807 - 12
Gaudin J.-M.Nikolaenko O.de Saint Laumer J.-Y.Winter B.Blanc P.-A. Helv. Chim. Acta 2007, 90: 1245 - 13
Lilienkampf A.Mao J.Wan B.Wang Y.Franzblau SG.Kozikowski AP. J. Med. Chem. 2009, 52: 2109 - 14
Murru S.Singh CB.Kavala V.Patel BK. Tetrahedron 2008, 64: 1931 - 15
Rao HSP.Vasantham K. J. Org. Chem. 2009, 74: 6847 - 16
Thoma G.Streiff MB.Kovarik J.Glickman F.Wagner T.Beerli C.Zerwes H.-Gn. J. Med. Chem. 2008, 51: 7915 - 17
Zhao Q.Liu S.Li Y.Wang Q. J. Agric. Food. Chem. 2009, 57: 2849 - 18
Alagille D.Koren AO.Kudej G.Staley J.Cosgrove K.Seibyl J.Tamagnan GD. J. Label. Comp. Radioph. 2008, 51: 202 - 19
Henry N.Sánchez I.Sabatié A.Bénéteau V.Guillaumet G.Pujol MD. Tetrahedron 2006, 62: 2405 - 20
Szabo Rm.Crozet MD.Vanelle P. Synthesis 2008, 127 - 21
Goubert M.Toupet L.Sinibaldi M.-E.Canet I. Tetrahedron 2007, 63: 8255 - 22
Isaka M.Ejiri S.Nakamura E. Tetrahedron 1992, 48: 2045 - 23
Bietti M.Capone A. J. Org. Chem. 2008, 73: 618 - 24
DePuy CH.Dappen GM.Eilers KL.Klein RA. J. Org. Chem. 1964, 29: 2813 - 25
Kochi JK.Singleton DM. J. Org. Chem. 1968, 33: 1027