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The Grieco elimination is an organic reaction describing the elimination reaction of an aliphatic primary alcohol through a selenide to a terminal alkene. [1] [2] It is named for Paul Grieco. The alcohol first reacts with o-nitrophenylselenocyanate and tributylphosphine to form a selenide via a nucleophilic substitution on the electron ...
Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. [1] The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
Formation of a secondary alcohol via alkene reduction and hydration is shown: The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with N-bromosuccinimide and water in halohydrin formation reaction. Amines can be converted to diazonium salts, which are then hydrolyzed.
In organic chemistry, the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene (R 2 C=CR 2) into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate (AcO−Hg−OAc) in aqueous solution to yield the addition of an acetoxymercury (−HgOAc) group and a hydroxy (−OH) group across the ...
A second significant side reaction in reactions of ketones and aldehydes is selanylation of the intermediate selenoxide. This process leads to elimination products retaining a carbon-selenium bond, [16] and is more difficult to prevent than the seleno-Pummerer reaction. Tertiary selenoxides, which are unable to undergo enolization, do not react ...
The hydroboration reaction is a useful reaction to functionalize alkenes to alcohols. In the reaction the trimethylsilyl (TMS) group fulfill 2 roles in directing the stereoselectivity of the reaction. First, the bulky size of TMS helped the molecule to preferably adopt a conformation where the TMS is not close to the methyl group on the alkene.
The Sharpless epoxidation is viable with a large range of primary and secondary alkenic alcohols. Furthermore, with the exception noted above, a given dialkyl tartrate will preferentially add to the same face independent of the substitution on the alkene.To demonstrate the synthetic utility of the Sharpless epoxidation, the Sharpless group created synthetic intermediates of various natural ...