The Disilylation of Styrene and α-Methylstyrene. The Trapping of Short-Lived Intermediates from Alkali Metals and Aryl Olefins¹

Alkali metal adducts of benzophenone azine. II. The lithium adduct

“…Again, the formation of a dilithium adduct of naphthalene in contrast to a mono sodium adduct may be cited (5). In situations more analogous to that under discussion, Weyenberg et al (6) have used lithium to obtain monomeric reduction products of aralkenes rather than their dimers. Smith and Veach (7) have cited this ability of lithium to explain the striking differences in behavior of acetophenone anil towards lithium and sodium.…”

The Reaction of Substituted Vinylsilanes with Lithium Metal

“…were in accordance with those reported in ref. [7] Ϫ C 24 H 34 (7), 131 (10), g (6.8 mmol) of 1,1-bis(trimethylsilyl)-2-phenylethene (42b) [27] in 10 ml of THF was added dropwise and the reaction mixture was 100 (8), 99 (76), 74 (9), 73 (100), 59 (7), 57 (6), 45 (10).…”

“…As stable intermediates in these reactions radical anions, like 7, can be observed, which are then reduced once again, here to the dianion 6. [6] These two types of reaction are analogous to the reductions of the corresponding styrene derivatives 1,1-diphenylethylene [7] and stilbene, [5a] obviously silyl groups have the same ability to stabilize negative charges in these polyanions as have aromatic substituents. The comparison holds even true for the structures observed for either 1,2-dilithio-1,1,2,2-tetrakis- thane (8), both show a double lithium bridge in trans configuration, interacting with the solvent (Figure 1).…”

trans-1,2,5-Triphenylsilacyclopentane

“…Prior syntheses to related compounds are described in Weyenberg, Toporcer & Bey (1965), Nefedov, Manalcov & Petrov (1961 and Gilman & Atwell (1964).…”