利用過量的 LiAlH4在加熱條件下還原醛酮的對(duì)甲苯磺?；甑玫酵闊N（或烯烴）的反應(yīng)。
利用此反應(yīng)還原3-膽甾酮可生成膽甾烷，還原α，β-不飽和酮可以得到烯烴，與此反應(yīng)類似的反應(yīng)有：Bamford–Stevens 和 Shapiro reaction。
此反應(yīng)相對(duì)于Wolff–Kishner還原反應(yīng)條件更加溫和，而且不用加堿，還原劑除了四氫鋁鋰，還有NaBH3CN，三乙酰氧基硼氫化鈉和兒茶酚硼烷，酯基，酰胺，腈，硝基，氯代物此反應(yīng)條件下都可以穩(wěn)定存在，但對(duì)溴代物和碘代物不耐受。
反應(yīng)機(jī)理
反應(yīng)實(shí)例
2-Methylnaphthalene (3). 2-Naphtalenecarboxaldehyde tosylhydrazone 2 (1 g) and LAH (1.5 g) in THF were refluxed for 12 h. Excess LAH was decomposed carefully with wet ether, the mixture was washed with dil H2SO4, dried and concentrated to give product 3 (70%).
【Caglioti R, Tetrahedron, 1963, 19, 1127】
【The Journal of Organic Chemistry. 40 (7): 923. doi:10.1021/jo00895a024】
【The Journal of Organic Chemistry. 41 (3): 574. doi:10.1021/jo00865a043】
【Organic Letters. 10 (2): 357–359. doi:10.1021/ol702921x】
相關(guān)文獻(xiàn)
1, Caglioti R, Tet Lett ,1962, 3, 1261
2, Caglioti R, Tetrahedron, 1963, 19, 1127
3, Combie RC, Aus J Chem, 1979, 32, 695
4, Shoppee CW, J Chem Soc Perkin 1, 1983, 2369
5, Toledano CA, Z Anorg Allg Chem, 2002, 628, 2104
6, Aleixo AM, Syn Comm, 2002, 32, 2937
參考文獻(xiàn)
一、Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 75-76.
二、維基百科：Wolff–Kishner reduction
