92172-52-6Relevant academic research and scientific papers
PHOTOCYCLOADDITION REACTIONS OF N-METHYLTHIOPHTHALIMIDE
Coyle, J. D.,Rapley, P. A.
, p. 2247 - 2248 (1984)
N-Methylthiophthalimide undergoes a photochemical cycloaddition reaction with 2,3-dimethylbut-2-ene or with stilbene to give products containing a spiro-thietane system; with 1,1-diphenylethene the product isolated is a diphenylmethyleneisoindoline.
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.
