92741-12-3Relevant academic research and scientific papers
Lithium Carbenoids Induced Ring Enlargement of Silicacyclobutane into 2-Halo-1-silacyclopentane and its Use in Organic Synthesis
Matsumoto, Kozo,Aoki, Yoshitaka,Oshima, Koichiro,Utimoto, Kiitiro
, p. 8487 - 8502 (2007/10/02)
An addition of lithium diisopropylamide to a solution of 1,1-dimethyl-1-silacyclobutane and dihalometane such as CH2I2, CH2Br2, or CH2Cl2 provided the corresponding 1,1-dimethyl-2-halo-1-silacyclopentane in good yield.The reactions of 1,1,2-trimethyl-1-si
Stereoselective formation of silacyclopentanes by the reaction of silacyclobutane with lithium carbenoids
Matsumoto, Kozo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 6055 - 6058 (2007/10/02)
An addition of lithium diisopropylamide to a solution of 1,1-dimethyl-1-silacyclobutane and diiodomethane provided 1,1-dimethyl-2-iodo-1-silacyclopentane in good yield.
Carbanion Rearrangements of ω-Phenyl-ω-(trimethylsilyl)alkyllithium Compounds: Intramolecular Reactions of Benzyltrimethylsilanes with a Carbon-Lithium Bond
Maercker, Adalbert,Stoetzel, Reinhard
, p. 1695 - 1706 (2007/10/02)
ω-Phenyl-ω-(trimethylsilyl)alkyllithium compounds show four out of five theoretically conceivable possibilities for intramolecular stabilization depending on the solvent and on the chain length n.While transmetalation of a methyl group at the silicon atom by a 1,(n+2) proton transfer is observed in any case, the intramolecular 1,n shift of the benzylic proton does only take place with n >/= 4.The main reaction, however for n = 3 and 4 only, is represented by the 1,n trimethylsilyl shift via a cyclic ate complex as an intermediate which partly splits off methyllithium yielding the corresponding silacycloalkane derivatives.In going from diethyl ether to THF as the solvent, the silyl shifts are more accelerated than the proton shifts.In no case, however, a Grovenstein-Zimmermann rearrangement involving phenyl migration took place.Degenerate silyl shifts starting from α-deuterated ω-(trimethylsilyl)alkyllithium compounds could not be detected either.Only by introduction of a second trimethylsilyl group into the 3 position a 1,3-(C -> C)-trimethylsilyl shift is initiated again.
RINGOEFFNUNG UND METALLIERUNG VON 1,1-DIMETHYL-2-PHENYL-SILACYCLOPENTAN UNTER DEM EINFLUSS VON METHYLLITHIUM IN TETRAHYDROFURAN
Maercker, Adalbert,Stoetzel, Reinhard
, p. C40 - C46 (2007/10/02)
In contrast to 1-phenylethyllithium, which reacts as a base, methyllithium attacks the silicon atom of 1,1-dimethyl-2-phenyl-silacyclopentane (7) as a nucleophile whereby ring-opening takes place presumably via an ate-complex intermediate.The primarily fo
