Consecutive Ring Closure and Neophyl Rearrangement of Some Alkenylaryl Radicals

Article abstract of DOI:10.1021/jo00227a024

The endo cyclization products 4a, 18a, 18b, 25b, and 25c obtained from the reaction of tributylstannane with the bromoarenes 1a, 12a, 12b, 22b, and 22c, respectively, are formed, at least in part, by exo cyclization of the corresponding substituted aryl radicals followed by neophyl rearrangement of the initial products.Kinetic data show that the rearrangement is more rapid for the radicals 15a and 15b containing the naphtalene nucleus than it is for the benzenoid radicals 24b and 24c and is facilitated by the presence of the electron-attracting substituent in 3a.