Some Reactions of N-Vinyl lmides on Vinyl and Carbonyl Moieties

Typical enimides such as N-vinylphthalimide 1, N-vinyl-o-sulfobenzimide (2), N-vinylsuccinimide 3, N-vinylcamphorimide [9], N-styrylphthalimide 10, cis- and trans-N, N'- vinylenediphthalimide 11 and [12] have been subjected to the following reactions on their vinyl and carbonyl groups with purpose of developing their synthetic uses. The Vilsmeier reaction on the vinyl group of 1 and 2 afforded N-(2-formylvinyl)imides, [6] and 7 (Table 1 and 2). Oxidation of 1-0 and 9, -12 with Mn(OAc)8 in acetic acid afforded imido-substituted butyrolactones, 13 19 (Table 3). The Grignard reaction on the carbonyl group of [1 ], [3] and [10] afforded N-vinyl hydroxy lactams (N-vinyl-3- hydroxy-1-isoindolinoes or N-vinyl-5-hydroxy-2-pyrrolidones), [20]-25 (Table 4 and 5). The Wittig reaction of [1], [3], (6) and [10] with triphenyl(ethoxycarbonylmethylene) phosphorane afforded N-vinyl-5-methylenelactams, [26]30 (Table 6). Reaction of 1, [2] and (3) with benzene in the presence of palladium in salt afforded 8-phenylated products, 10 and [33], and/or 1, 4-bis(imido)butadienes (dimerized products), 31 and [32] (Table 7).