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

Journal of the Brazilian Chemical Society

Luiz F. Silva Jr.¹  Eliane C. Pedrozo¹  Helena M. C. Ferraz¹ 

[1] ,Universidade de São Paulo Instituto de Química São Paulo SP ,Brazil

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

DOI  :  10.1590/S0103-50532006000100029

来源: SciELO

【 摘 要 】

The rearrangement of beta,gamma-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 beta-keto ester moiety, which would be useful for further functionalization.

【 授权许可】

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