The reaction of [1.1.1]propellane with singlet methylene afforded 1,3-dimethylenecyclobutane and [l.1.1.1]paddlane (3). Various minor products were also produced. The reaction of [1.1.1]propellane with triplet methylene afforded 1,3-dimethylenecyclobutane (2) and various minor products. But even trace of [1.1.1.1]paddlane was not detected. The mechanism for the addition of singlet methylene involved [1.1.1.1]paddlane intermediate The addition of triplet methylene led to diradical intermediate. In order to reveal the reaction pathway for generation of various ruiner products, various studies were carried out under the same condition.