Toward a molecular-size "Tinkertoy" construction set. Preparation of terminally functionalized [n]staffanes from [1.1.1]propellane

Article abstract of DOI:10.1021/ja00028a029

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.