Rearrangement of beta,gamma-unsaturated esters with thallium trinitrate: synthesis of indans bearing a beta-keto ester moiety

Journal of the Brazilian Chemical Society

Silva Jr., Luiz F.¹  Pedrozo, Eliane C.¹  Universidade de São Paulo, São Paulo, Brazil¹  Ferraz, Helena M. C.¹ 

关键词: indan;    ring contraction;    thallium trinitrate;    b-keto ester;   

DOI  :  10.1590/S0103-50532006000100029

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

The rearrangement of b,g-unsaturated esters, such as 2-(3,4-dihydronaphthalen-1-yl)-propionic acid ethyl ester, with thallium trinitrate (TTN) in acetic acid leads to 3-indan-1-yl-2-methyl-3-oxo-propionic acid ethyl ester in good yield, through a ring contraction reaction. The new indans thus obtained feature a b-keto ester moiety, which would be useful for further functionalization.

【 授权许可】

Unknown