"Treatment of an alkene with mercuric acetate in aqueous THF results in the electrophilic addition of mercuric ion to the double bond to form an intermediate mercurium ion. Nucleophilic attack by H2O at the more substituted carbon yields a stable organomercury compound, which upon addition of NaBH, undergoes reduction. Replacement of the carbon-mercury bond by a carbon-hydrogen bond during the reduction step proceeds via a radical process. The overall reaction represents Markovnikov hydration of a double bond, which contrasts with the hydroboration-oxidation process."
Quote Details
Added by wikiquote-import-bot
Unverified quote
0 likes
Original Language: English
Available Languages (1)
Sources
George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 5 : Functional Group Transformations: The Chemistry of Carbon-Carbon π-Bonds and Related Reactions.
https://en.wikiquote.org/wiki/Oxymercuration_reaction
Revision History
No revisions have been submitted for this quote.
Categories
Oxymercuration reaction
2 quotes on TrueQuotesView all quotes by Oxymercuration reaction →
Related Quotes
"In the laboratory, alkenes are often hydrated by the oxymercuration–demercuration procedure. … Alkene oxymercuration …"
"MnO2 is a highly chemoselective oxidant—allylic, benzylic, and propargylic alcohols are oxidized faster than saturate…"
"CrO2·C5H5N is a mild reagent for the oxidation of alcohols that contain acid-sensitive groups. … Primary and secondar…"
"The Swern oxidation proceeds rapidly at low temperatures and thus can be employed for the preparation of a-keto aldeh…"
"The most utilized Umpolung strategy is based on formyl and acyl anion equivalents derived from 2-lithio- 1,3-dithiane…"
"The classical procedure for oxidizing primary alcohols to aldehydes and secondary alcohols to ketones involves treatm…"
"The Jones reagent is an excellent reagent for the oxidation of secondary alcohols that do not contain acid-sensitive …"
"The carbonyl group is electrophilic at the carbon atom and hence is susceptible to attack by nucleophilic reagents. T…"
"Domino-type reactions involve careful design of a multistep reaction in a one-pot sequence in which the first step cr…"
"Umpolung in a synthesis usually requires extra steps. Thus, one should strive to take maximum advantage of the functi…"