Rhodium(I)-catalysed skeletal reorganisation of benzofused spiro[3.3]heptanes via consecutive carbon-carbon bond cleavage

Skeletal reorganisation of benzofused spiro[3.3]heptanes has been achieved using rhodium(I) catalysts. The reaction of benzofused 2-(2-pyridylmethylene)spiro[3.3]heptanes proceeds via sequential C-C bond oxidative addition and beta-carbon elimination. On the other hand, benzofused spiro[3.3]heptan-2-ols undergo two consecutive beta-carbon elimination processes. In both cases, substituted naphthalenes are obtained.