Highly Strained Cage Compounds from a Fourfold Bridged Tricyclo[4.2.0.0^2,5]octa‐3,7‐diene

Abstract

The fourfold bridged tricyclo[4.2.0.02~5]octa-3,7-diene derivative 3 reacts with diazomethane and m-chloroperbenzoic acid (mCPBA) to yield the monoadduct 5 in good and the bisadduct 4 in poor yield as well as the mono-and bisepoxides 7 and 8 in good yields, respectively. Also the "mixed product 6 is obtained. All five compounds are strained propellanes. The Xray crystallographic structure analysis of 8 reveals a distance of 2.812 A between the epoxide rings.Cage compounds have fascinated chemists for many They are not only appealing because of their usually high symmetry but also represent versatile model compounds. Due to their rigid geometry they are used as models for cycloaddition reactions, for the study of long-range interactions and for the investigation of the geometrical conditions for electron transfer, to name only a few examples. Chem.