Journal of the Brazilian Chemical Society
Print version ISSN 0103-5053
On-line version ISSN 1678-4790
SILVA JR., Luiz F.; PEDROZO, Eliane C. and FERRAZ, Helena M. C.. Rearrangement of b,g-unsaturated esters with thallium trinitrate: synthesis of indans bearing a b-keto ester moiety. J. Braz. Chem. Soc. [online]. 2006, vol.17, n.1, pp.200-205. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532006000100029.
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.
Keywords : indan; ring contraction; thallium trinitrate; b-keto ester.