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Dehalogenation using Grignard reagents is a two steps hydrodehalogenation process. The reaction begins with the formation of alkyl/arene-magnesium-halogen compound, followed by addition of proton source to form dehalogenated product.
In it, Zaytsev proposed a purely empirical rule for predicting the favored regiochemistry in the dehydrohalogenation of alkyl iodides, though it turns out that the rule is applicable to a variety of other elimination reactions as well. While Zaytsev's paper was well referenced throughout the 20th century, it was not until the 1960s that ...
Dehydrohalogenation to give an alkene In chemistry , dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate . The reaction is usually associated with the synthesis of alkenes , but it has wider applications.
The scope of the Corey-House synthesis is exceptionally broad, and a range of lithium diorganylcuprates (R 2 CuLi, R = 1°, 2°, or 3° alkyl, aryl, or alkenyl) and organyl (pseudo)halides (RX, R = methyl, benzylic, allylic, 1°, or cyclic 2° alkyl, aryl, or alkenyl and X = Br, I, OTs, or OTf; X = Cl is marginal) will undergo coupling as the nucleophilic and electrophilic coupling partners ...
Using a carboxylate-to-iodine ratio of 1:1 leads to an alkyl iodide product, in line with Borodin's findings and the modern understanding of the Hunsdiecker reaction. However, a 2:1 ratio favours the formation of an ester product that arises from decarboxylation of one carboxylate and coupling the resulting alkyl chain with the other. [9] [10]
The iodide anion is a good nucleophile and will displace chloride, tosylate, bromide and other leaving groups, as in the Finkelstein reaction. Alcohols can be converted to the corresponding iodides using phosphorus triiodide. Illustrative is the conversion of methanol to iodomethane: [15] PI 3 + 3 CH 3 OH → 3 CH 3 I + "H 3 PO 3 "
In a related chemical test, known as the Herzig–Meyer alkimide group determination, a tertiary amine with at least one methyl group and lacking a beta-proton is allowed to react with hydrogen iodide to the quaternary ammonium salt which when heated degrades to methyl iodide and the secondary amine.
The Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. [1] The use of carbon tetrabromide or bromine as a halide source will yield alkyl bromides, whereas using carbon tetraiodide, methyl iodide or iodine gives alkyl iodides.