95840-10-1Relevant academic research and scientific papers
PHOTOREACTIONS OF PHTHALIMIDE-THIETANES: FISSION OF THE THIETANE RING AND FORMATION OF 1,2-DITHIANES
Machida, Minoru,Oda, Kazuaki,Yoshida, Eiichi,Kanaoka, Yuichi
, p. 147 - 156 (2007/10/02)
Photolysis of N-methylmonothiophthalimide (1) in the presence of thietane (4) gave 1,2-dithiane (5) and 1,3-dithiane (6).The formation of 1,2-dithianes in the photoreaction of 1 with styrene derivatives (2) is explained in terms of the intermediacy of the phthalimide-thietanes.Photolysis of the thietane ring is also described.
PHOTOREACTION OF N-SUBSTITUTED MONOTHIOPHTHALIMIDES WITH STYRENE DERIVATIVES. AN EXAMPLE OF FORMATION AND FISSION OF THIETANE RING.
Machida, Minoru,Oda, Kazuaki,Yoshida, Eiichi,Kanaoka, Yuichi
, p. 4691 - 4700 (2007/10/02)
Photolysis of N-methylmonothiophthalimide (1) in the presence of various styrene derivatives (2) afforded efficiently spiro-thietanes (3).The stereochemistry and the chemical conversion of the thietanes were discussed.
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.
Photochemistry of the Thioimide Systems: Imide-Thietanes
Machida, Minoru,Oda, Kazuaki,Yoshida, Eiichi,Kanaoka, Yuichi
, p. 1681 - 1688 (2007/10/02)
General photochemical behavior of cyclic thioimides, nitrogen-thiocarbonyl systems, was studied.The dithioimides were inert to the Norrish type I and II reactions in contrast to the behavior of their oxygen analogues (imides) and nitrogen-lacking counterparts (thiones).However, various aliphatic and aromatic di- and monothioimides underwent intermolecularly efficient photocycloaddition with olefins to afford the imide-thietanes in good yields.
PHOTOCYCLOADDITION REACTIONS OF N-METHYLTHIOPHTHALIMIDE
Coyle, J. D.,Rapley, P. A.
, p. 2247 - 2248 (2007/10/02)
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.
