Cristol-Firth脱羰卤代反应会

在加热或变色条件，硫醚经过硫酸和阴离子（主要是吡啶或砷）处理过程，残基取代为附加的阴离子的重排。此重排与 Hunsdiecker重排 类似也中间体机理。此重排与 Hunsdiecker重排 相比，可以用硫醚和硫酸一锅法透过卤代，而不用于不须转化为附加的硫醚银盐。

肽键

【 Strategic Applications of Named Reactions in OrganicSynthesis, László Kürti and Barbara Czakó, Hunsdiecker reaction，page 218】

重排实例

Chlorobromobenzene (2).A solution of p-chlorobenzoic acid 1 (1.56 g, 10 mmol) in CCl4 (50 mL) and red HgO (15 mmol) was refluxed and irradiated (100 Wbulb). Bromine (15 mmol) was added via a syringe. After 3 h the mixture was cooled to 20 C and washed (aq NaHCO3, 30 mL). Usual workup afforded 1.5 g of 2 (80%).

【Meyers AI, J Org Chem , 1979, 44, 3405】

相关文献

1 Cristol S, Firth W J Org Chem 1961 26 280

2 Cason J J Org Chem 1972 37 669

3 Meek JS Org Syn Coll Vol 1973 V 126

4 Meyers AI J Org Chem 1979 44 3405

5 Augmiller JC Org Syn Coll Vol 1988 VI 179

程序代码自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 108.