Stepwise oxidation of the stannole dianion.

Tin oxidation of stannole dianion 1 with 1.3 equivalents of oxygen gave terstannole-1,3-dianion 3. The non-aromatic nature of 3 was confirmed by X-ray crystallographic analysis.

Reversible redox behavior between stannole dianion and bistannole-1,2-dianion.

The reversible redox behavior between the stannole dianion and the bistannole-1,2-dianion is demonstrated. Reaction of the stannole dianion with oxygen (1 eq) gives the 1,2-bistannole-1,2-dianion which is a tin-analogue of the cyclopentadienyl anion in 94% yield. Reaction of the stannole dianion with ferrocenium tetrafluoroborate (1 eq) also gives the 1,2-dianion.

Silyl migration in the photochemical reactions of 2-trimethylsilylmethylphenyl ketones.

[reaction: see text]. Irradiation of 2-trimethylsilylmethylphenyl ketones 1 gives benzocyclobutenols 2 and 5 together with siloxybenzocyclobutenes 4. Compound 4 arises from the novel photoinduced 1,5-silyl migration of 1.

Formation of the first monoanion and dianion of stannole.

The first syntheses of mono- and dianions of stannole were accomplished by transmetallation or reduction of the novel bi(1,1-stannole).