[1.1.1]Paddlane has an inverted structure at two bridge-head carbon atoms. We will describe the reaction of [1.1.1]Propellane and [22.214.171.124]Paddlane. The reaction of [1.1.1]propellane with singlet methylene affored 1.3-Dimethylene as the major product and [126.96.36.199]paddlane as the minor products were obtained. The reaction of [1.1.1]propellane with triplet methylene was carried out in the similar condition. The result afforded 1,3-Dimethylenecylopropane as the major product and various side products were also obtained. But no trace of [188.8.131.52]paddlane was detected. After the synthesis of [184.108.40.206]paddlane, continuously [220.127.116.11]paddlane reacts with iodide. The product that I expected for 1.3-diiodo-tricyclo[18.104.22.168]hexane is different, and has unsymmetrical structure.