Photochemicalreactions of 2-(pentamethyldisilanyl)furan and 2-(pentamethyldigermanyl)furan have been investigated by chemical trapping experiments and laser flash-photolysis. On irradiation, the furylated catenates of Group 14 elements undergo silicon-silicon σ bond and germanium-germanium σ bond homolysis to give a pair of silyl radicals and germyl radicals, respectively. In CCl4, these radicals
highly cytotoxic 1‐3‐[1‐(5‐organylsilyl‐furan‐2‐yl)silinan‐1‐yl]propyl}amines and sometrimethylgermylanalogues (IC50 1–7 μg mL−1) have been synthesized by a hydrosilylation reaction of aliphatic and heterocyclic N‐allylamines in the presence of Speier’s catalyst. The effects of the silacycle, the element‐organic substituent in position 5 of the furan ring, and the structure of the amine on the cytotoxicity
involved electrophilicsubstitution of hydrogen atoms in position 5 or 3 of the furan ring. The alkylation reaction and bromination with DDB occur via ipso-substitution of the trialkylgermyl group. Dichlorocarbene generated by phase-transfer catalysis adds to the 2-germyl-substituted furan at the C4C5 bond in the ring. Some of the above reactions were conducted with trimethyl(2-furyl)silane and 2-(t-butyl)furan