137335-17-2Relevant academic research and scientific papers
Toward a molecular-size "Tinkertoy" construction set. Preparation of terminally functionalized [n]staffanes from [1.1.1]propellane
Kaszynski, Piotr,Friedli, Andrienne C.,Michl, Josef
, p. 601 - 620 (2007/10/02)
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.
REACTIONS 0F PROPELLANE
Zefirov, N. S.,Surmina, L. S.,Sadovaya, N. K.,Blokhin, A. V.,Tyurekhodzhayeva, M. A.,et al.
, p. 2002 - 2014 (2007/10/02)
The photochemical reactions of propellane with bromine, dioxane dibromide, iodine, (dichloroiodo)benzene, methyl iodide, carbon tetrabromide, bromoform, and tributyltin hydride take place by a radical mechanism and lead to the formation of the products from addition at the central bond, i.e., 1,3-substituted bicyclopentanes.In the photochemically initiated reactions of chloroform, carbon tetrachloride, and bromomalonic ester with propellane compounds with the structure of 1,1'-bis(bicyclopentane) are formed in significant amounts in addition to the above-mentioned compounds.The addition of hydrogen bromide with irradiation leads to the brominated derivatives of cyclopropane and cyclobutane.The formation of cyclobutane derivatives is also observed in the reactions with such reagents as bromine or dioxane bromide (with irradiation) and 2-nitrobenzenesulfenyl chloride (in the presence of atmospheric oxygen).In the course of the reaction of propellane with electrophilic reagents (mercuric acetate, tripropyl- and triallylboranes) ring cleavage occurs, and derivatives of methylenecyclobutane are formed.
