120853-58-9Relevant academic research and scientific papers
Chemistry of Substituted (2-Butene-1,4-diyl)magnesium: A Facile Approach to Complex Carbocycles, Functionalized Ketones and Alcohols, and Silicon-Containing Heterocycles
Rieke, Reuben D.,Xiong, Heping
, p. 3109 - 3118 (2007/10/02)
Highly reactive magnesium reacts with a wide variety of substituted 1,3-dienes to give the corresponding substituted (2-butene-1,4-diyl)magnesium complexes.Reactions of symmetrical (2-butene-1,4-diyl)magnesium with α,ω-alkylene dihalides form three-, four-, five-, and six-membered carbocycles.Significantly, the cyclizations are always stereospecific and completely regioselective.Depending on the initial 1,3-diene and specific electrophiles, uncyclized products can be obtained.Stepwise reactions of (2,3-dimethyl-2-butene-1,4-diyl)magnesium with two different electrophiles afford polyfunctionalized ketones with the generation of a quaternary center.Formal 1,2-additions can be effected in this manner.Substituted five- and six-membered cyclic ketones can also be synthesized in one step by this approach.Treatment of unsymmetrical (2-butene-1,4-diyl)magnesium complexes with triorganosilyl chlorides followed by cyclohexanone results in additions across a terminal double bond with high regioselectivity.Silicon-containing heterocycles or spiro compounds can be readily synthesized by using the bis-Grignard reagents.
Reduction of (E,E)-(η6:η6-1,4-Diphenyl-1,3-butadiene)bis(tricarbonylchromium), Followed by Reaction with Electrophiles. A Regioselective Method for the Preparation of Substituted 1,4-Diphenylbutenes
Rieke, Reuben D.,Daruwala, Khushroo P.,Forkner, Matthew W.
, p. 21 - 24 (2007/10/02)
Reduction of (E,E)-(η6:η6-1,4-diphenyl-1,3-butadiene)bis(tricarbonylchromium) with lithium naphthalenide followed by reaction with alkyl halides and acyl chlorides yields, after oxidative cleavage of the tricarbonylchromium groups, dialkylated and diacylated 1,4-diphenylbutenes.
