89745-98-2

Upstream product

• 56068-50-9 2,2-dimethylhex-5-en-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 116911-84-3 5-chloro-5-methyl-1-hexene 
• 58203-68-2 2,2-dimethylhex-5-enoic acid 
• 73062-97-2 ethyl 1-but-3-en-1-ylcyclohexanecarboxylate 

Downstream Products

• 7116-86-1 5,5-dimethyl-hex-1-ene 
• 97467-22-6 [(E)-1-(2,2-Dimethyl-hex-5-enyloxy)-propenyl]-benzene 

Relevant academic research and scientific papers

Competing Radical, Carbanion, and Carbene Pathways in the Reactions of Hindered Primary Alkyl Halides with Lithium Dialkylamides

A variety of methods were utilized to study the mechanism of reaction of 6-iodo-5,5-dimethyl-1-hexene and its bromo, chloro, and tosylate derivatives with LDA and several other lithium dialkylamides.In the reaction of 6-iodo-5,5-dimethyl-1-hexene with LDA in THF, radical, carbanion, and carbene pathways occured simultaneously.However, when the corresponding bromide was allowed to react with LDA, the radical pathway was minor and when the corresponding chloride or tosylate was allowed to react with LDA, no evidence for radical products was observed.This is the first time that competing radical, carbanion, and carbene pathways have been detected in the reaction of a primary alkyl halide with any nucleophile.

Occurrence of Electron Transfer in the Reduction of Organic Halides by LiAlH4 and AlH3

A variety of methods have been utilized to detect the occurrence of a single electron transfer pathway in the reduction of alkyl halides by LiAlH4 and AlH3, i.e., (1) product studies of reduction of cyclizable alkyl halides containing the 5-hexenyl group, (2) trapping of intermediate radicals by dicyclohexylphosphine and other trapping agents, (3) direct EPR observation of the trityl radical in the reduction of trityl bromide, and (4) stereochemical studies of the reduction of secondary halides by lithium aluminum deuteride.The extent of electron transfer was found to be a function of the solvent, the substrate, the leaving group, and the hydride reagent.For alkyl iodides, and to a lesser extent bromides, electron transfer was found to be the major reaction pathway; however, no evidence for electron transfer was found for the corresponding chlorides or tosylates.Reduction of (+)-2-octyl iodide by LiAlD4 was found to be much less stereospecific than the corresponding reduction of bromide, chloride, or tosylate, indicating intermediate radical formation in the reduction of the secondary iodide.