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The decarboxylation of this compound by heat is essential for the psychoactive effect of smoked cannabis, and depends on conversion of the enol to a keto group when the alpha carbon is protonated. Upon heating, Δ9-tetrahydrocannabinolic acid decarboxylates to give the psychoactive compound Δ9- Tetrahydrocannabinol . [ 13 ]
Here decarbonylation accompanies the preparation of cyclopentadienyliron dicarbonyl dimer: 2 Fe(CO) 5 + C 10 H 12 → (η 5 −C 5 H 5) 2 Fe 2 (CO) 4 + 6 CO + H 2. Decarbonylation can be induced photochemically as well as using reagents such as trimethylamine N-oxide: Me 3 NO + L + Fe(CO) 5 → Me 3 N + CO 2 + LFe(CO) 4
The crystal structures of the THF complexes of the Reformatsky reagents tert-butyl bromozincacetate [25] and ethyl bromozincacetate [26] have been determined. Both form cyclic eight-membered dimers in the solid state, but differ in stereochemistry: the eight-membered ring in the ethyl derivative adopts a tub-shaped conformation and has cis bromo groups and cis THF ligands, whereas in the tert ...
Benzene is an organic chemical compound with the molecular formula C 6 H 6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.
Dehydration may be accompanied by decarboxylation when an activated carboxyl group is present. The aldol addition product can be dehydrated via two mechanisms; a strong base like potassium t -butoxide , potassium hydroxide or sodium hydride deprotonates the product to an enolate , which eliminates via the E1cB mechanism , [ 9 ] [ 10 ] while ...
The alpha-ketol rearrangement is an interconversion of a hydroxyl alpha to a carbonyl to the complementary carbonyl and hydroxyl groups, with migration of a substituent. It is mechanistically equivalent to the benzyllic acid rearrangement at the point after the nucleophile attacks the 1,2-dicarbonyl.
The intramolecular version of ketonic decarboxylation is often called the Ružička large-ring synthesis (or Ružička cyclization), named for Lavoslav Ružička who developed the technique from prior methods that could synthesize small cyclic compounds from calcium salts of dicarboxylic acids. [10]
Thus, synthesis of benzaldehyde through the Friedel–Crafts pathway requires that formyl chloride be synthesized in situ. This is accomplished by the Gattermann-Koch reaction, accomplished by treating benzene with carbon monoxide and hydrogen chloride under high pressure, catalyzed by a mixture of aluminium chloride and cuprous chloride ...