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- Title
Photochemistry of Isothiocoumarin (= 1 H-[2]benzothiopyran-1-one).
- Authors
Bethke, John; Kopf, Jürgen; Margaretha, Paul; Pignon, Bernard; Dupont, Léon; Christiaens, Léon E.
- Abstract
Irradiation (λ = 350 nm) of 1 H-[2]benzothiopyran-1-one ( 2) in the solid state affords selectively and in good yield 6aα, 6bα, 12bα, 12cα -tetrahydrocyclobuta[1, 2- c:4, 3- c′]bis([2]benzothiopyran)-5, 8-dione ( 3), the head-to-head (HH) cis- cisoid- cis-cyclodimer of 2, X-Ray analysis of 2 confirms that this reaction proceeds according to the well-established topochemical principles. The same dimer 3 is obtained in low yields on irradiation of 10−1 M solutions of 2 in either MeOH or MeCN, while no conversion at all is observed in benzene. On irradiation of 2 in MeCN in the presence of tetrachloroethene, the [2 + 2] photocycloadduct 4 is formed in good yield, the conversion 2 → 4 being efficiently quenched by naphthalene. In contrast, no reaction is observed -on irradiation of 2 in the presence of 2, 3-dimethylbut-2-ene, neither in polar nor in apolar solvents.
- Publication
Helvetica Chimica Acta, 1997, Vol 80, Issue 6, p1865
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19970800610