Julia-Bruylants环丙基甲醇重排

环丙基甲醇及其衍生物在酸催化下重排为高烯丙基卤代物（通常为E构型烯烃）的反应。环丙基环氧乙烷也可以进行此反应。

反应机理

反应实例

5-(g-Bromopropylidene)-5H-dibenzo[a,d-]10,11-dihydrocycloheptene (6). 15% HBr in HOAc (10 mL) was added at 10 C with stirring to 1.3 g (5.19 mmol) of cyclopropyl carbinol 5 in 20 mL glacial HOAc. After 30 min at 10 C, filtration, washing (H2O) and air drying afforded 730 mg of 6, mp 71–72 C. Upon addition of H2O to the filtrate, 800 mg more of 6 was obtained, total yield 98%.

【Wendler NL, J Org Chem, 1962, 27, 4134】

相关文献

1 Bruylants P Bull Acad Royal Belg 1928 14 140

2 Julia M Bull Soc Chim Fr 1960 1072

3 Julia M Bull Soc Chim Fr 1961 1849

4 Wendler NL J Org Chem 1962 27 4134

5 Julia M Tetrahedron Suppl 1966 443

6 Corey EJ J Org Chem 1967 32 4160

7 Johnson WS J Am Chem Soc 1968 90 2882

8 Faulkner J Synthesis 1971 175

9 Nakamura H Tet Lett 1973 14 111

10 Kocienski PJ Chem Ind 1981 548

11 Ranu BC Eur J Org Chem 2006 3012

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 240.