Results on the synthesis of silocanes and germocanes, eight-membered heterocycles with the general formula D(CH 2 CH 2 Z) 2 MXY are analyzed and classified. The chemical behavior of these compounds and the characteristics of the element-nitrogen transannular bond are studied.Metallocanes include eight-membered heterocyclic compounds with the general formula D(CH 2 CH 2 Z) 2 MX k Y n (k, n = 0-2), in which transannular interaction is possible between the atom of the metal (metalloid) M and the heteroatom D containing an unshared electron pair. Such derivatives are known for a large number of elements (M = B, Si, Ge, Sn, Pb, As, Sb, Bi, transition metals). Among the compounds formed by the atoms of nontransition elements the metallocanes of group 14 (mainly derivatives of silicon and germanium) have been investigated most.In the present article the currently available data on the synthesis and reactivity of silocanes and germocanes and on the physicochemical investigation of the compounds are reviewed. The review includes data on compounds in which the central group 14 atom forms four covalent bonds and is capable of forming one or two additional intramolecular hypervalent interactions. A major contribution to the development of the chemistry of these derivatives was made by several research groups led by E. Lukevics, M. Voronkov, V. Mironov, V. D'yakov, A. Tzschach and K. Jurkschat, J. Corey, M. Gilen, R. Holmes, and M. Dräger. It is also necessary to mention a recent review on the metallocanes of heavy elements of groups 14 and 15 [1].