NUCLEOPHILIC ADDITIONS TO STYRENE AND DERIVATIVES

M. Montserrat Martínez, M. Gabriela Ónega, Julio A. Seijas*, M. Pilar Vázquez- Tato*

Departamento de Química Orgánica. Facultad de Ciencias.
Universidad de Santiago de Compostela. Aptdo. 280.
27080-Lugo. Spain.



Previous work: 

     We have reported that alkyllithiums1 and lithium amides2 reacted with o-vinylphenyloxazolines to give addition products in good yields (scheme 1). It is also known that styrene suffers addition of alkyllithiums to the exocyclic double bond.3

Results: 

     Here, we studied the influence that the absence of the oxazoline group could have in the course of the reaction. We did our experiments with a carboxyl group instead and we observed lower yields than with the oxazoline group in the ring (scheme 2).

     We studied as well reaction of lithium morpholide with o- carboxystyrene (scheme 3) and with styrene itself (scheme 4).

Conclusions: 




Acknowledgments

Financial support form Spanish DGICYT (PB93-0647) is gratefully acknowledged.

References:

  1. J. A. Seijas, M. P. Vázquez-Tato, J. Org. Chem, 1992, 57, 5283
  2. J. A. Seijas, M. P. Vázquez-Tato, et al. Communications to the 36th. IUPAC Congress. Geneva, august 17-22, 1997.
  3. X. Wei, J. K. Taylor, Chem. Commun., 1996, 187