TOWARD A MOLECULAR-SIZE TINKERTOY CONSTRUCTION SET - PREPARATION OF TERMINALLY FUNCTIONALIZED [N]STAFFANES FROM [1.1.1]PROPELLANE

A facile but low-yield synthesis of [n] staffanes (the oligomers of [1.1.1] propellane 1, n = 1-5) functionalized on one or both ends is described, and their properties are summarized. The substituents are -COOCH3, -n-C4H9, -C6H5, -Br, -I, and -SCOCH3, and their conversion to others, such as -COOH, -COCH3 and -SH, is demonstrated. It is proposed that these rod-shaped molecules will be useful in the development of a molecular-size civil engineering construction set analogous to children's toy construction sets.