六氯环己-2,5-二烯-1-酮（Hexachlorocyclohexa-2,5-dien-1-one ），一种高效的氯化试剂，可以用于各种氯化反应，具有空间选择性。

与此类似的化合物还有2,3,5,6-四溴-4-甲基-4-硝基-环己-2,5-二烯酮是一种基本上没有氧化性的温和的硝化试剂，可用于带有游离氨基的芳香化合物的硝化。

【Lemaire. M, Tetrahedron, 1987, 43 (5), 835】

反应实例

1-Hydroxychloronaphtalenes (4, 5). 3 (720 mg, 5 mmol) in stirred DMF (10 mL) was treated at 20 C with 2 (301 mg, 5 mmol). After 48 h, the mixture was concentrated and chromatographed (Al2O3, heptane:EA 7:3). Purification by chromatography on silica gel (heptane:EA) gave 0.8 g of 4 + 5 (99%), ratio of o-:p- 30:70.

【Guy A, Lemaire M, Guette JP, Tetrahedron, 1982, 38, 2354】

2,3,5,6-Tetrabromo-4-methyl-4-nitro-2,5-cyclohexadien-1-one (2.34 g, 5 mmol) was added to the solution of 2-Bromo-4-fluoro-phenylamine (0.95 g, 5mmol) in dry THF (40 mL). The mixture was stirred for 2 h at room temperature. The solvent was removed under reduced pressure and the residue was purified by column chromatography to give the desired product (0.82 g, 70%).

【Lemaire. M, Tetrahedron, 1987, 43 (5), 835】

相关文献

1 Guy A, Lemaire M, Guette JP Tetrahedron 1982 38 2346

2 Guy A, Lemaire M, Guette JP Tetrahedron 1982 38 2354

3 Messmer A Tetrahedron 1986 42 5415

4 Guy A, Lemaire M, Guette JP Jansen Chim Acta 1987 5 3

5 Guy A, Lemaire M, Guette JP Tetrahedron 1987 43 835

6 Khatinzadeh G Acta Chim Slov 2007 54 284

7 Ready JM J Am Chem Soc 2011 133 9956

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 196.