107978-17-6Relevant articles and documents
Photochemical Cycloaddition Reactions of N-Methyl(thiophthalimide) and N-Methyl(dithiophthalimide) with Alkenes
Coyle, John D,Rapley, Patricia A
, p. 2273 - 2278 (2007/10/02)
Irradiation of N-methyl(thiophthalimide) with alkenes leads to reaction at the thiocarbonyl, rather than at the carbonyl, group of the thioimide.Products isolated include (2+2) cycloadducts (isoindole-1-spiro-2'-thietanes), a cleavage product (a 3-alkylideneisoindol-1-one) derived from such cycloadducts, or (2+2+2) cycloadducts incorporating two molecules of thioimide (1,4-dithiane-2,3-bis-spiroisoindoles).The products are consistent with a mechanism that involves an intermediate 1,4-biradical, and they contrast markedly with those obtained from N-methylphthalimide with alkenes. N-Methyl-(dithiophthalimide) is less effective in photoreactions with alkenes, and in only one instance was a cycloadduct formed at a reasonable rate and isolated; possible reasons for this difference are discussed.