Reduction of Halomethanes with Lithium Aluminum Hydride
نویسنده
چکیده
A study has been made of t he reactions of lithium aluminum hydride with methyl bromide, methylene chloride, meth ylene bromide, methylene iodide, chloroform, bromoform, and carbon t etrachloride. Except for hydrogen and unreacted h alida, essentia lly pure methane was formed in each case. The amount of hydrogen evolved increased with the n umber of halogen atoms in the molecule, reaching a maximum in the reduction of carbon t etrachloride. This fact , together \\·ith t he absence of hydrocarbons heav ier t han methane, indicate that t he reaction proceeds by a step-wise process raLher t han a silTl.ultan eous stripping of several haloge n atoms [rOITl t he molecule .
منابع مشابه
Reexamination of Aluminum Hydride as a Stereoselective Reducing Agent for Reduction of Cyclic Ketones to Thermodynamically More Stable Alcohols
Aluminum hydride, a very interesting and valuable reducing agent, has been widely used in numerous applications in organic syntheses. Jorgenson first reported the comparison in the reducing properties between lithium aluminum hydride and aluminum hydride on the reduction of cinnamaldehyde, and Brown and Yoon reported a systematic study on the reducing properties of aluminum hydride in THF. Fina...
متن کاملReductions of Carboxylic Acid Derivatives
Reductions of carboxylic acid derivatives might be expected to lead either to aldehydes or alcohols, functional groups having a lower oxidation state of the carboxyl carbon. that carboxylic acids themselves are reduced to alcohols by lithium aluminum hydride. At this point it will be useful to consider three kinds of reductions: (i) catalytic hydrogenation (ii) complex metal hydride reductions ...
متن کاملPreparation of Precocene 2 and 3 , 4 - Epoxyprecocene 2 Deuterated Analogues at C - 3 , C - 4 and C - 3 , C - 4
Precocene Analogues, Deuteration A convenient route for the preparation of title compounds from benzopyran-4-one (1) and its corresponding 3,3-H2 deuterated analogue (2) is reported. Treatment of 1 or 2 with lithium aluminum deuteride followed by dehydration afforded, respectively, 4-H precocene (3c) or 3,4-H2 precocene (3b). Likewise, reduction of 2 with lithium aluminum hydride and subsequent...
متن کاملA Twist on Facial Selectivity of Hydride Reductions of Cyclic Ketones: Twist-Boat Conformers in Cyclohexanone, Piperidone, and Tropinone Reactions
The role of twist-boat conformers of cyclohexanones in hydride reductions was explored. The hydride reductions of a cis-2,6-disubstituted N-acylpiperidone, an N-acyltropinone, and tert-butylcyclohexanone by lithium aluminum hydride and by a bulky borohydride reagent were investigated computationally and compared to experiment. Our results indicate that in certain cases, factors such as substrat...
متن کاملRapid reductive-carboxylation of secondary amines, one pot synthesis of N'-(4-11C-methyl)imipramine.
A new rapid high yield synthesis of radiolabeled N'-(4-11C-methyl)imipramine has been developed using a reductive-carboxylation approach, in which 11CO2 is reacted with either N'-trimethylsilyldesimipramine or N'-lithium derivative of desimipramine, followed by lithium aluminum hydride reduction, to give no carrier added or carrier added 11C-labeled imipramine respectively. The final product is...
متن کامل