7-alkylcycloalkano (Dewar benzene^).^ These compounds were expected to constitute an interesting extension of the" Dewar benzene chemistry" reported so far. In this paper we report the synthesis of the tetramethyl-1, 4-tetramethylene (Dewar benzene)(2, a [4.2. 2] propella-7, 9-diene) 5i8 as well as its conversion into the tricyclic ketone 3 (a [4.3. 2] propella- 7, 10-dien-9-one). Furthermore, ketone 3 has been shown to be a suitable substrate for an ...