Distorted to Pentacoordinated Carbon- Convex Platonic Molecular Relationships

This review includes insights into the structures and strain energies of tetrahedrane, cubane, and dodecahedrane and their derivatives. Cubane and dodecahedrane are stable. Tetrahedrane has eluded even transitory observation. Tetra-tert-butyltetrahedrane, stabilized sterically, and a number of silyl and related derivatives, stabilized sterically and electronically, are isolable molecules. Substituted derivatives of cubane include the perfluoro derivative, one-electron reduction of which produces “an electron in a box”. Octanitrocubane and heptanitrocubane are high explosives. The electron affinity of perfluorododecahedrane is comparable to that of F2. Derived polybrominated trienes provide access to C20 fullerene. There is brief mention of octahedral C6 and icosahedral C12.