The Experts below are selected from a list of 27 Experts worldwide ranked by ideXlab platform
William J. Moore - One of the best experts on this subject based on the ideXlab platform.
-
Oxidative rearrangement of sulfur-containing tertiary allylic alcohols: synthesis of 2-cycloalkenones bearing 3-[(phenylthio)methyl] and 3-[2-alkyl-1,3-dithian-2-yl] substituents
Journal of Organic Chemistry, 1993Co-Authors: Frederick A. Luzzio, William J. MooreAbstract:Substrate 1-[(phenylthio)methyl]-2-cycloalkenols 3a-d and 1-[2-alkyl-1,3-dithian-2-yl]cyclohexenols 1a-a were prepared by adding [(phenylthio)methyl]lithium and 2-lithio-2-alkyl-1,3-dithianes, respectively, in the 1,2-mode to various 2-cycloalkenones. The ranges of yields for the additions were 86-96% in the (phenylthio)methyl series and 69-88% in the dithiane series. A representative compound from each range of substrate tertiary allylic alcohols was then treated with a series of oxochromium(VI)-amine Reagents such as pyridinium chlorochromate (PCC), pyridinium dichromate (PDC), the Collins Reagent (CrO 3 .Pyr 2 ), and 2,2'-bipyridinium chlorochromate (BPCC)
David Zhigang Wang - One of the best experts on this subject based on the ideXlab platform.
-
Reductive and Transition-Metal-Free: Oxidation of Secondary Alcohols by Sodium Hydride
Journal of the American Chemical Society, 2010Co-Authors: Xinbo Wang, Bo Zhang, David Zhigang WangAbstract:The oxidation of alcohols into their corresponding carbonyl compounds represents a fundamentally important functional group transformation and occupies a prominent position in modern synthetic organic chemistry. Advances on the development of new oxidation Reagents and methodologies and their applications in both targetand diversity-oriented synthesis have been regularly surveyed and constituted one of the most extensively and actively investigated areas of current organic synthesis. In this context, a plethora of oxidants, including those small organic molecule-based Reagents (such as Dess-Martin periodinane, Swern oxidation, Moffatt oxidation, Corey-Kim oxidation, and SO3/pyridine) and metal-based systems (such as Jones Reagent, Collins Reagent, pyridinium chlorochromate, pyridinium dichromate, barium permanganate, manganese dioxide, ruthenium tetroxide, silver carbonate, and Oppenauer oxidation), have been identified to be powerful tools promoting conversion of various alcohols into their corresponding aldehyde or ketone products and thus evolved as a most important class of tools in synthetic chemists’ arsenal. A recent conceptually novel approach in alcohol oxidation chemistry, driven by the needs of process environmental compatibility and sustainability, has been exploring aerobic oxidation with highly active transition-metal catalysts (such as Pd, Ru, Fe, Cu, Pt, Au, Ir, Rh, etc.) and dioxygen gas as the terminal oxidant, their heterogeneously immobilized variants, and biomimetic systems. Despite these impressive advances, very few of the known methods are capable of offering truly economic and practical oxidation transformations across a broad spectrum of alcohol substrates. Many of these systems suffered from high Reagent cost, air instability, employment of heavy metals or organic oxidants, stringent reaction conditions, operational complexity, functional group incompatibility, or production of wastes in their related processes. Thus, there is a continuing and increasing demand for new Reagents that could help address the above-mentioned challenges. We herein report on an exceedingly simple secondary alcohol oxidation protocol that employs the widely available sodium hydride (NaH) as the oxidant.
Frederick A. Luzzio - One of the best experts on this subject based on the ideXlab platform.
-
Oxidative rearrangement of sulfur-containing tertiary allylic alcohols: synthesis of 2-cycloalkenones bearing 3-[(phenylthio)methyl] and 3-[2-alkyl-1,3-dithian-2-yl] substituents
Journal of Organic Chemistry, 1993Co-Authors: Frederick A. Luzzio, William J. MooreAbstract:Substrate 1-[(phenylthio)methyl]-2-cycloalkenols 3a-d and 1-[2-alkyl-1,3-dithian-2-yl]cyclohexenols 1a-a were prepared by adding [(phenylthio)methyl]lithium and 2-lithio-2-alkyl-1,3-dithianes, respectively, in the 1,2-mode to various 2-cycloalkenones. The ranges of yields for the additions were 86-96% in the (phenylthio)methyl series and 69-88% in the dithiane series. A representative compound from each range of substrate tertiary allylic alcohols was then treated with a series of oxochromium(VI)-amine Reagents such as pyridinium chlorochromate (PCC), pyridinium dichromate (PDC), the Collins Reagent (CrO 3 .Pyr 2 ), and 2,2'-bipyridinium chlorochromate (BPCC)
Xinbo Wang - One of the best experts on this subject based on the ideXlab platform.
-
Reductive and Transition-Metal-Free: Oxidation of Secondary Alcohols by Sodium Hydride
Journal of the American Chemical Society, 2010Co-Authors: Xinbo Wang, Bo Zhang, David Zhigang WangAbstract:The oxidation of alcohols into their corresponding carbonyl compounds represents a fundamentally important functional group transformation and occupies a prominent position in modern synthetic organic chemistry. Advances on the development of new oxidation Reagents and methodologies and their applications in both targetand diversity-oriented synthesis have been regularly surveyed and constituted one of the most extensively and actively investigated areas of current organic synthesis. In this context, a plethora of oxidants, including those small organic molecule-based Reagents (such as Dess-Martin periodinane, Swern oxidation, Moffatt oxidation, Corey-Kim oxidation, and SO3/pyridine) and metal-based systems (such as Jones Reagent, Collins Reagent, pyridinium chlorochromate, pyridinium dichromate, barium permanganate, manganese dioxide, ruthenium tetroxide, silver carbonate, and Oppenauer oxidation), have been identified to be powerful tools promoting conversion of various alcohols into their corresponding aldehyde or ketone products and thus evolved as a most important class of tools in synthetic chemists’ arsenal. A recent conceptually novel approach in alcohol oxidation chemistry, driven by the needs of process environmental compatibility and sustainability, has been exploring aerobic oxidation with highly active transition-metal catalysts (such as Pd, Ru, Fe, Cu, Pt, Au, Ir, Rh, etc.) and dioxygen gas as the terminal oxidant, their heterogeneously immobilized variants, and biomimetic systems. Despite these impressive advances, very few of the known methods are capable of offering truly economic and practical oxidation transformations across a broad spectrum of alcohol substrates. Many of these systems suffered from high Reagent cost, air instability, employment of heavy metals or organic oxidants, stringent reaction conditions, operational complexity, functional group incompatibility, or production of wastes in their related processes. Thus, there is a continuing and increasing demand for new Reagents that could help address the above-mentioned challenges. We herein report on an exceedingly simple secondary alcohol oxidation protocol that employs the widely available sodium hydride (NaH) as the oxidant.
Michael E. Johnson - One of the best experts on this subject based on the ideXlab platform.
-
OXIDATION OF CERTAIN 4-SUBSTITUTED PHENETHYL ALCOHOLS WITH Collins Reagent: ON THE MECHANISM OF A CARBON-CARBON BOND CLEAVAGE
Synthetic Communications, 1995Co-Authors: Michael E. JohnsonAbstract:Abstract A mechanism is proposed for a carbon-carbon bond cleavage observed in the oxidation of certain 4-substituted phenethyl alcohols with Collins Reagent.