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Communication | Special issue | Vol 35, No. 1, 1993, pp.63-67
Published online, 1st January, 1970
DOI: 10.3987/COM-92-S25
Regioselectivity in the 1,3-Dipolar Cycloaddition Reaction of Diazomethane to 7-Oxanorbornene Derivatives

Odón Arjona,* Cristina Manzano, and Joaquín Plumet*

*Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, Ciudad Universitaria, E-28040 Madrid, Spain

Abstract

The regioselectivity of the 1,3-dipolar cycloaddition reaction of diazomethane to 7-oxabicyclo[2.2.l]hept-5-ene derivatives substituted on C-2 is discussed. The observed ratio of regioisomers depends upon the nature of the substituents on C-2 and may be accounted for in terms of TS asyncrony for concerted processes.