"Target molecules containing a 1,4-cyclodhexadiene unit are probably best prepared via the Birch reaction. These primary reduction synthons can be further elaborated into a variety of synthetically useful compounds … Isomerizations of l,4-cyclohexadienes with KOt-Bu in DMSO furnish the thermodynamically more stable conjugated 1,3-cyclohexadienes. … Hydrolysis of the initial enol ether (vinyl ether) formed from Birch reduction of anisole or substituted anisoles under mild acidic con- ditions leads to β,γ-unsaturated cyclohexenones. Under more drastic acidic condi- tions, these isomerize to the conjugated α,β-cyclohexenones. Birch reduction of anisoles followed by hydrolytic workup is one of the best methods available for preparing substituted cyclohexenone. It should be noted that Birch reduction of 4-substituted anisoles followed by acidic workup (aq HCl, THF) produces mixtures of isomeric cyclohexenones. … Selective cleavage of the more nucleophilic double bond of anisole-derived 1,4-cyclohexadienes by ozone provides highly function- alized acyclic compounds containing a stereodefined double bond. … Birch reduction-alkylation of benzoic acids and esters establishes quaternary carbon centers. Neighboring stereocenters will influence the stereochemical outcome of the tandem reaction sequence."
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/Birch_reduction
Revision History
No revisions have been submitted for this quote.
Categories
Related Quotes
"Alkali metals in liquid ammonia in the presence of an alcohol reduce aromatic systems to 1,4-cyclohexadienes. These c…"
"The reduction is initiated by addition of a solvated electron to the aromatic system to generate a radical anion, whi…"
"Birch reduction of substrates containing methoxy or N,N-dimethylamino groups may be contaminated with appreciable amo…"
"Birch reduction of monosubstituted benzenes could furnish either of two possible 1,4-cyclohexadienes … Generally, ele…"
"MnO2 is a highly chemoselective oxidant—allylic, benzylic, and propargylic alcohols are oxidized faster than saturate…"
"The Jones reagent is an excellent reagent for the oxidation of secondary alcohols that do not contain acid-sensitive …"
"The Swern oxidation proceeds rapidly at low temperatures and thus can be employed for the preparation of a-keto aldeh…"
"Umpolung in a synthesis usually requires extra steps. Thus, one should strive to take maximum advantage of the functi…"
"Domino-type reactions involve careful design of a multistep reaction in a one-pot sequence in which the first step cr…"
"The classical procedure for oxidizing primary alcohols to aldehydes and secondary alcohols to ketones involves treatm…"