Abstract Condensation of 1, 1-dimethyl-3, 4-diphenyl-2, 5-bis (p-tolylhydroxymethyl) silole with pyrrole and p-tolylaldehyde did not form the expected 21, 21-dimethyl-2, 3-diphenyl-5, 10, 15, 20-tetra (p-tolyl)-21-silaporphyrin, but rather its reduced derivative, 21-silaphlorin, which contains a tetrahedrally hybridised C5 carbon atom. Attempts to trap 21-silaporphyrin resulted in the serendipitous discovery of a unique transformation of 21-silaphlorin into a ...