哈米克反應
哈米克反應（英語：Hammick reaction），得名於英國化學家達爾齊爾·哈米克，指在羰基化合物存在下，α-吡啶甲酸及其類似物受熱轉變為2-吡啶基原醇。[1][2][3]
反應機理
[編輯]加熱時，α-吡啶甲酸發生脫羧，生成兩性離子(2)。該離子與強親電試劑（如醛）作用，發生對羰基的親核加成。加成產物發生質子轉移，便得到原醇(4)。
參見
[編輯]參考資料
[編輯]- ^ Dyson, P.; Hammick, D. L. 362. Experiments on the mechanism of decarboxylation. Part I. Decomposition of quinaldinic and isoquinaldinic acids in the presence of compounds containing carbonyl groups. J. Chem. Soc. 1937: 1724. doi:10.1039/jr9370001724.
- ^ Hammick, D. L.; Dyson, P. 172. The mechanism of decarboxylation. Part II. The production of cyanide-like ions from α-picolinic, quinaldinic, and isoquinaldinic acids. J. Chem. Soc. 1939: 809. doi:10.1039/jr9390000809.
- ^ Brown, E. V.; Shambhu, M. B. Hammick reaction of methoxypyridine-2-carboxylic acids with benzaldehyde. Preparation of methoxy-2-pyridyl phenyl ketones. J. Org. Chem. 1971, 36: 2002. doi:10.1021/jo00813a034.
- ^ Sperber, N.; Papa, D.; Schwenk, E.; Sherlock, M. Pyridyl-Substituted Alkamine Ethers as Antihistaminic Agents. J. Am. Chem. Soc. 1949, 71: 887. doi:10.1021/ja01171a034.