944347-68-6Relevant academic research and scientific papers
The reactivity of epoxides with lithium 2,2,6,6-tetramethylpiperidide in combination with organolithiums or grignard reagents
Hodgson, David M.,Fleming, Matthew J.,Stanway, Steven J.
, p. 4763 - 4773 (2008/02/04)
(Chemical Equation Presented) The scope and limitations of lithium 2,2,6,6-tetramethylpiperidide (LTMP)-modified reductive alkylation of epoxides is detailed. A variety of organolithiums are added to terminal and 2,2-disubstituted epoxides in the presence of LTMP to generate alkenes in a completely regio- and highly stereoselective manner. Arylated alkenes, dienes, allylsilanes, and enynes are accessed using this procedure. The methodology is applied in the synthesis of the roller leaf moth pheromone, (3E,5Z)-dodecadienyl acetate. The corresponding reaction without LTMP has also been examined, and a study using deuterated epoxides provides insight into the mechanism. In the presence of LTMP, Grignard reagents are also shown to produce E-alkenes directly from epoxides.
Chromium Tricarbonyl Complexes of Dimethyl(phenyl)allylsilanes and their Treatment with Fluoride Ion
Fleming, Ian,Sanderson, Philip E. J.,Zammattio, Francoise
, p. 1020 - 1025 (2007/10/02)
Chromiumtricarbonyl complexation of the phenyl ring of allyldimethyl(phenyl)silanes enhances the rate of protodesilylation of both the phenyl ring and the allyl group.
