双α-卤代丁二酸酯通过氰化钠取代后得到α-氰基酯负离子中间体，接着进行分子内亲核取代得到环丁烷-1,2-二羧酸酯的反应。

反应操作

Diethyl 3-methyl-2-cyano-1,2-cyclobutanedicarboxylate (3). Diethyl a,a‘-dibromo-β-methyladipate 1 (20 g, 55 mmol) and powdered NaCN (8 g, 160 mmol) in abs EtOH (15 mL) were heated to reflux for 24 h to give after filtration of salts and evaporation of the solvent 8 g of 3 (63%), bp 140–143 ℃/3 mm.

【Fuson RC, J Am Chem Soc., 1930, 52, 4074】

相关文献

1 Franchimond APN Chem Ber 1872 5 1049

2 Zelinsky N Ber 1888 21 3160

3 Fuson RC J Am Chem Soc 1929 51 1536

4 Fuson RC J Am Chem Soc 1930 52 4074

5 Henecka H Ber 1950 176

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 162.