Theoretical study of the reaction mechanism and migratory aptitude of the pinacol rearrangement

No abstract is available for this paper.

• Publication year

  1993

• Venue

  Journal of the American Chemical Society

• Publication date

  1993-10-01

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1021/JA00073A029
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• No references are available for this paper.

• A combined experimental and density functional theory investigation of the reaction between β-Nitrostyrene and trimethylsilyl cyanide

  2025cites this paper
• Chemoselectivity in Pd-Based Dyotropic Rearrangement: Development and Application in Total Synthesis of Pheromones.

  2024cites this paper
• Experimental verification of halomethyl carbinol synthesis from carbonyl compounds using a TiCl4–Mg bimetallic complex promoter

  2024cites this paper
• Stepwise or Concerted Mechanisms? Rethinking of the Classical Carbocation Rearrangement Reaction

  2024cites this paper
• Asymmetric Bromination/Semipinacol Rearrangement Enabled by Brønsted Acids of Stereogenic-at-Cobalt(III) Complexes.

  2024cites this paper
• Highly Efficient One-Pot Synthesis of 2,4,5-Trisubstituted 3(2H)-Furanones Utilizing a Au(I)-Catalyzed Oxidation/Pinacol Rearrangement/anti-Michael Cascade.

  2024cites this paper
• Vapor Phase Cross Ketonization of Pivalic Acid with Acetic Acid to Prepare Pinacolone Over Mg-Zr Mixed Oxide Catalysts

  2024cites this paper
• One-Carbon Homologation of Knoevenagel Adducts: Enantioselective Access to Benzhydryl Derivatives.

  2024cites this paper
• Semipinacol Rearrangement of Cyclopropenylcarbinols for the Synthesis of Highly Substituted Cyclopropanes.

  2023cites this paper
• Disproportionation-Inspired Construction of Highly Functionalized Bicyclo[3.2.1]octanes.

  2023cites this paper
• Scale-Up of Synthesizing 3,3-Dimethyl-2-butyl Ketone (Pinacolone) from 2-Methyl-2-butene (β-Isoamylene) and Its Kinetic Study

  2023cites this paper
• Evidence for the Chemical Mechanism of RibB (3,4-Dihydroxy-2-butanone 4-phosphate Synthase) of Riboflavin Biosynthesis

  2022cites this paper
• A boryl-migratory semipinacol rearrangement

  2022cites this paper
• Removal of C3–C4 diols in ethylene glycol via selective dehydration reactions over Beta zeolite with acidity tailored

  2022cites this paper
• Methyl ethyl ketone

  2022cites this paper
• Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope, and Limitations

  2021cites this paper
• Unexpected Domino Silyl-Prins/Aryl Migration Process from Geminal Vinylsilyl Alcohols

  2021cites this paper
• The unusual migratory aptitude in a case of α-carbonyl cation-driven 1,2-migration

  2020cites this paper
• Effect of Mixed-Solvent Environments on the Selectivity of Acid-Catalyzed Dehydration Reactions

  2020cites this paper
• Rearrangement Reactions

  2020cites this paper
• Michael addition of amines to sterically crowded ortho-benzoquinone completed with unprecedented 1,2-shift of a tert-butyl group

  2020cites this paper
• Silica-supported orthophosphoric acid (OPA/SiO2): preparation, characterization, and evaluation as green reusable catalyst for pinacolic rearrangement

  2019cites this paper
• Unexpected Vinylcyclopropane Rearrangement: New Strategies toward Skipped Dienes Using Sulfonium Ylides

  2019cites this paper
• A Brønsted Acid Catalyzed Tandem Pinacol-Type Rearrangement for the Synthesis of α-(3-Indolyl) Ketones by Using α-Hydroxy Aldehydes.

  2019cites this paper
• Piers' borane-mediated hydrosilylation of epoxides and cyclic ethers.

  2018cites this paper
• Tuning the Selectivity: Study of Solvent-Free Acid-Mediated Pinacolic-Pinacolone Rearrangement under Microwave Irradiation

  2018cites this paper
• Asymmetric Synthesis of Cyclobutanone via Lewis Acid Catalyzed Tandem Cyclopropanation/Semipinacol Rearrangement.

  2018cites this paper
• Mechanistic Insights into a Chiral Phosphoric Acid-Catalyzed Asymmetric Pinacol Rearrangement.

  2018cites this paper
• Mechanistic Investigation of a Novel Medium-Sized Ring Rearrangement

  2017cites this paper
• Conceptual design for the recovery of 1,3-Butadiene and methyl ethyl ketone via a 2,3-Butanediol-dehydration process

  2017cites this paper
• Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products.

  2017cites this paper
• Catalytic Reductive Pinacol-Type Rearrangement of Unactivated 1,2-Diols through a Concerted, Stereoinvertive Mechanism.

  2017cites this paper
• Development of an Efficient Asymmetric Synthesis of the Chiral Quaternary 5-Lipoxygenase Activating Protein Inhibitor

  2016cites this paper
• Kinetic Model Development for Dehydration of 2,3-Butanediol to 1,3-Butadiene and Methyl Ethyl Ketone over an Amorphous Calcium Phosphate Catalyst

  2016cites this paper
• Influence of basicity on 1,3-butadiene formation from catalytic 2,3-butanediol dehydration over γ-alumina

  2016cites this paper
• 2,3-Butanediol dehydration catalyzed by silica-supported sodium phosphates

  2016cites this paper
• Intermolecular Reactions of a Foiled Carbene with Carbonyl Compounds: The Effects of Trishomocyclopropyl Stabilization.

  2015cites this paper
• Catalysis of diazoalkane-carbonyl homologation. How new developments in hydrazone oxidation enable the carbon insertion strategy for synthesis.

  2015cites this paper
• Highly stereoselective oxazaborolidinium ion catalyzed synthesis of (Z)-silyl enol ethers from alkyl aryl ketones and trimethylsilyldiazomethane.

  2014cites this paper
• Studies on [PtCl2 ]- or [AuCl]-catalyzed cyclization of 1-(Indol-2-yl)-2,3-allenols: the effects of water/steric hindrance and 1,2-migration selectivity.

  2014cites this paper
• Brönsted Acid of Keggin Type Polyoxometalate Catalyzed Pinacol Rearrangement

  2014cites this paper
• 3.16 The Semipinacol Rearrangements

  2014cites this paper
• Fe-catalyzed regiodivergent [1,2]-shift of α-aryl aldehydes.

  2013cites this paper
• Migration of methylethynyl group in a long-lived carbocation.

  2013cites this paper
• A combined theoretical and experimental investigation into the highly stereoselective migration of spiroindolenines.

  2013cites this paper
• Scope and Post‐Transformations for the Borane‐Isocyanide Multicomponent Reactions: Concise Access to Structurally Diverse Heterocyclic Compounds

  2013cites this paper
• The para-substituent effect and pH-dependence of the organometallic Baeyer-Villiger oxidation of rhenium-carbon bonds.

  2012cites this paper
• DFT and experimental exploration of the mechanism of InCl3-catalyzed type II cycloisomerization of 1,6-enynes: identifying InCl2(+) as the catalytic species and answering why nonconjugated dienes are generated.

  2012cites this paper
• Rapid and efficient protic ionic liquid-mediated pinacol rearrangements under microwave irradiation

  2011cites this paper
• Acids and Acid Catalysis – Homogeneous

  2011cites this paper
• Reactions Involving Hypercarbon Intermediates

  2011cites this paper
• Biomimetic Formation of 2‐Tropolones by Dioxygenase‐Catalysed Ring Expansion of Substituted 2,4‐Cyclohexadienones

  2010cites this paper
• Reaction pathway of aliphatic pinacol‐type rearrangement reexamined

  2010cites this paper
• Geminal acylation of α-heterosubstituted cyclohexanones and their ketals

  2010cites this paper
• Pinacol-type rearrangement catalyzed by Zr-incorporated SBA-15

  2010cites this paper
• Degenerate rearrangement of long-lived 9-cyclopropyl-9,10-dimethyl-9,10-dihydrophenanthren-9-ylium: Migration of cyclopropyl group

  2010cites this paper
• Al Lewis acid-catalyzed regiodivergent 1,2-rearrangement of α-siloxy aldehydes: scope and mechanism

  2009cites this paper
• Recent advances in the semi-pinacol rearrangement of α-hydroxy epoxides and related compounds

  2007cites this paper
• Theoretical study of the role of solvent H2O in neopentyl and pinacol rearrangements

  2007cites this paper
• Isoxazole-directed pinacol rearrangement: stereocontrolled approach to angular stereogenic centers.

  2007cites this paper
• Is phenyl a good migrating group in the rearrangement of organoborates generated from sulfur ylides?

  2006cites this paper
• Charge density analysis of some processes involving intramolecular hydrogen transfer

  2005cites this paper
• A density functional study of propylene glycol conversion to propanal and propanone of various acid‐catalyzed reaction models: A water‐addition effect

  2005cites this paper
• Toward the enantioselective total synthesis of lyngbyatoxin A: on the stereocontrolled introduction of the quaternary stereogenic centre

  2003cites this paper
• Fe-substituted molecular sieves as catalysts in liquid phase pinacol rearrangement

  2002cites this paper
• Effect of various acids at different concentrations on the pinacol rearrangement

  2002cites this paper
• Cell biology and molecular basis of denitrification.

  1997cites this paper
• Acid promoted rearrangement of PCU-derived pinacols

  1995cites this paper
• 1,2-Carbon to nitrogen migrations. Part 2. Ab initio study on the rearrangement of (α-methylazo)alkyl isocyanates

  1994cites this paper
• Migratory aptitude of hydrogen and stabilization of the transition-state by the non-migrating substituent in 1,2-migrations to electron deficient nitrogen

  1994cites this paper