Skip to main content
SpringerLink
Log in

Photocycloaddition of 2-benzoylthiophene to methylmaleic anhydrides

Photocycloaddition von 2-Benzoylthiophen an Methylmaleinsäureanhydride

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

Upon direct irradiation with light of wavelengths greater than 300 nm, 2-benzoylthiophene undergoes [2 + 2] cycloadditions withmono- anddi-methylmaleic anhydrides involving the C=C bond of the latter and the benzoyl-substituted thiophene C=C bond.

Zusammenfassung

Aus 2-Benzoylthiophen entstehen unter direkter Bestrahlung mit Licht von Wellenlängen > 300 nm in Anwesenheit von Methylmaleinsäureanhydriden [2 + 2]-Cycloaddukte. Die Photoreaktion erfolgt an den C=C-Bindungen des Thiophenrings und des Anhydrids.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Rivas C, Payo E, Cortes L (1968) Photochem Photobiol7: 807

    Google Scholar 

  2. Rivas C, Krestonosich S, Payo E, Cortes L (1970) Acta Científica Venezolana21: 28 (1970) Chem Abst73: 24636v

    Google Scholar 

  3. Rivas C, Velez M, Crescente O (1970) Chem Commun 1474

  4. Rivas C, Velez M, Crescente O, Flores SE (1971) Rev Latinoaméricana de Quim,2: 9; (1971) Chem Abst75: 140596x

    Google Scholar 

  5. Rivas C, Nakano T, Pérez C (1975) Rev Latinoaméricana de Quim6: 166; (1976) Chem Abst84: 120785r

    Google Scholar 

  6. Rivas C, Pacheco D, Vargas F (1980) J Heterocycl Chem17: 1151

    Google Scholar 

  7. Pacheco D, Rivas C, Vargas F (1983) J Heterocycl Chem20: 1465

    Google Scholar 

  8. Rivas C, Vargas F, Torrealba A, Pacheco D, Machado R, Aguiar G (1994) Monatsh Chemie125: 1153

    Google Scholar 

  9. Rivas C, Bolivar RA (1973) J Heterocycl Chem10: 967

    Google Scholar 

  10. Cantrell T (1972) Chem Commun155; Cantrell T (1974) J Org Chem39: 2242

  11. Turro NJ, Wriede PA (1969) J Org Chem34: 3562

    Google Scholar 

  12. Turro NJ (1969) In: Lamola AA, Turro NJ (eds) Energy transfer and organic photochemistry. Techniche of organic chemistry, vol XIV. [Leermakers PA, Weissberger A (eds)] Inter Science Publishers, New York London Sydney Toronto, pp 202 and 211

    Google Scholar 

  13. Leon V, Bolivar RA, Tasayco ML, González R, Rivas C (1983) Org Magn Reson21: 470

    Google Scholar 

  14. Arnold DR, Birtwell RJ (1973) J Am Chem Soc95: 4599; Arnold DR, Birtwell JJ, Clarke BM, Clarke JR (1974) Can J Chem52: 1681

    Google Scholar 

  15. Bolivar RA, González R, Machado R, Rivas C, Tasayco ML (1986) J Photochem32: 363

    Google Scholar 

  16. Griesbeck AG, Stadtmüller S (1991) J Am Chem Soc113: 6923

    Google Scholar 

  17. Schenck GO, Hartmann W, Mannsfeld S-P, Metzner W, Krauch CH (1962) Chem Ber95: 1642; Bryce-Smith D, Bullen GJ, Clark NH, Connett BE, Gilbert A (1966) J Chem Soc (c) 167

    Google Scholar 

  18. Boule P, Lamaire J (1978) J Chem Phys75: 1

    Google Scholar 

  19. Flores SE, Velez M, Rivas C (1971) Org Mass Spec5: 1049

    Google Scholar 

  20. Vogel AI (1956) Practical organic chemistry, 3rd. edn. Love and Brydone, London, p 969

    Google Scholar 

  21. Nakano T, Rivas C, Perez C, Tori K (1973) J Chem Soc PerkinI: 2322 and references therein

Download references

Author information

Author notes

  1. R. A. Bolivar

    Present address: INTEVEP, Los Teques, Venezuela

Authors and Affiliations

  1. Centro de Química, Instituto Venezolano de Investigaciones Científicas I.V.I.C., 1020-A, Caracas, Venezuela

    C. Rivas, R. A. Bolivar, R. González, R. Machado & F. Vargas

Authors
  1. C. Rivas
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. A. Bolivar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. González
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. Machado
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. F. Vargas
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rivas, C., Bolivar, R.A., González, R. et al. Photocycloaddition of 2-benzoylthiophene to methylmaleic anhydrides. Monatsh Chem 127, 529–536 (1996). https://doi.org/10.1007/BF00807078

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00807078

Keywords

Search

Navigation