Iminyl radicals by stannane mediated cleavage of oxime esters

Article abstract of DOI:10.1016/S0040-4039(00)76523-3

Despite the explosive growth in the use of radical reactions which has swept organic synthesis in the past few years, nitrogen centred radicals and iminyls in particular have not yet attracted the attention they deserve This can be traced to a large extent to a lack of convenient and mild methods for generating such species. As part of a general study of the reactivity and synthetic potential of iminyls, we recently showed that the reaction of sulfenimines with tributystannane or the Barton decarboxylation of O-carboxymethyl oximes represented useful routes to these intermediates. Another promising approach, still in its preliminary stages however, involved the reduction of oxime esters with nickel powder in acetic acid. in this Letter, we describe yet another method based on the cleavage of oxime benzoates with tin centered radicals.