Synthesis of Heptacyclo[7.7.0.0/2,6/0/3,15/0/4,12/0/5,10/0/11,16]-Hexadeca-7,13-Diene - a Novel Dimer of Barrelene Possessing Perpendobiplanar D2d Symmetry

Abstract

The synthesis of heptacyclo [7.7.0.0^2,6.0^3,15.0^4,12.0^5,10.0^11,16]hexadeca-7,13- diene (9) is described. The diene (9) was obtained in three steps from the known diketone heptacyclo -[6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14] tetradecane - 7,12-dione (5). Double ring expansion of (5) (with diazomethane) gave (12). Conversion of (12) into-the bis ( tosylhydrazone ), followed by double Bamford -Stevens rearrangement, gave the diene (9).