Summary
The benzophenone sensitized photocycloaddition of 2,3-dimethylmaleimide to selenophene and 3,4-dimethylselenophene was carried out first to generalize the photoaddition reaction of methylmaleic anhydride derivatives to selenophene, using this time the nitrogen analogue, and second to reexamine the composition of the product mixture formed in the reaction. It was found that in adition to the 1:1 adduct isolated in previous investigations, three geometrical isomers may be proposed for the 2:1 adduct (two molecules of maleimide of one of selenophene or its methyl derivative).
Zusammenfassung
Die benzophenonsensitivierte Photocycloaddition von 2,3-Dimethylmaleimid an Selenophen und 3,4-Dimethylselenophen wurde durchgeführt, um erstens die Photoadditionsreaktionen von Methylmaleinsäureanhydridderivaten an Selenophen allgemein zu studieren und um zweitens die Zusammensetzung der bei der Reaktion gebildeten Produktgemische erneut zu untersuchen. Zusätzich zu dem bei früheren Arbeiten gefundenen 1:1-Addukt werden drei geometrische Isomere für das 2:1 — Addukt (2 Moleküle Maleimid und 1 Molekül Selenophen oder 3,4-Dimethylselenophen) vorgeschlagen.
Similar content being viewed by others
References
Rivas C., Pacheco D., Vargas F. (1980) J. Heterocyclic Chem.17: 1151
Nakano T., Rivas C., Pérez C., Tori K. (1973) J. Chem. Soc., Perkin Trans.I: 2322
Leon V., Bolivar R. A., Tasayco M. L., Gonzalez R., Rivas C. (1983) Org. Magnetic Res.21: 470
Flores S. E., Velez M., Rivas C. (1971) Org. Mass Spectrom.5: 1049
Pacheco D., Rivas C., Vargas F. (1983) J. Heterocyclic Chem.20: 1465
Fringuelli F., Taticchi A. (1978) J. Heterocyclic Chem.15: 137
Rivas C., Pérez C., Nakano T. (1975) Rev. Latinoam. Quim.6: 166; Chem. Abs. (1976)84: 120785r
Gronowitz S., Frejd T. (1976) J. Heterocyclic Chem.13: 1319
Barbey G., Dian G., Merlet N., Outurquin F., Paulmier C. (1986) Synthesis 181
Organic Synthesis coll. Vol. 1 (1958) Wiley, New York, p. 457
Satisfactory analytical data (C, H, N, Se) were obtained for the reported compounds
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Rivas, C., Vargas, F., Torrealba, A. et al. Photocycloaddition of 2,3-dimethylmaleimide to selenophene and 3,4-dimethylselenophene. Monatsh Chem 125, 1153–1158 (1994). https://doi.org/10.1007/BF00811523
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00811523