腈被氯化亚锡/HCl气体还原，通过形成Sn-醛亚胺络合物，水解得到醛的反应。

反应机理

反应实例

Phenylacetaldehyde (7). Dry HCl gas was passed for 2 h with stirring into anhyd SnCl2 (57 g, 0.3 mol in 400 mL dry ether) to form a separate viscous layer. Freshly distilled 6 (16 g, 0.136 mol) was added with vigorous stirring for 1 h. After the mixture stood for 18 h, 2 slowly separated and after 5 h the ether was decanted and the residue washed with dry ether. Water (800 mL) and NaHCO3 (till neutral to congo red) were added to the residue. The mixture was boiled and steam was passed through until the total volume of distillate was 250 mL. Extraction with ether and workup afforded 5.4 g, 33% of 7, bp 87–88 C.

【Williams JW, J Am Chem Soc., 1939, 61, 2248】

相关文献

1 Stephen J J Chem Soc 1925 127 1874

2 Williams JW J Am Chem Soc 1939 61 2248

3 Ferguson LW Chem Rev 1946 38 243

4 Mosettig E Org React 1954 8 246

5 Stephen TW J Chem Soc 1956 4695

6 Tolbert J J Org Chem 1963 28 696

7 Markaryan EA Armen Khim Zhu 1974 27 878

8 Voloboev SN Russ J Gen Chem 2001 71 1121

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 456.

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由腈制备醛酮