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在加熱或光照條件,羧酸經過氧化汞和鹵素(主要是溴或碘)處理,羧基取代為相應的鹵素的反應。此反應與類似也自由基機理。此反應與相比,可以用羧酸和氧化汞一鍋法進行鹵代,而不用于先轉化為相應的羧酸銀鹽。
反應機理
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【Strategic Applications of Named Reactions in OrganicSynthesis, László Kürti and Barbara Czakó, Hunsdiecker reaction,page 218】
反應實例
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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】
相關文獻
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
編譯自:Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 108.
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