Open Access. Powered by Scholars. Published by Universities.®

Physical Sciences and Mathematics Commons™

Open Access. Powered by Scholars. Published by Universities.®

Organic Chemistry

Selected Works

2004

Articles 1 - 5 of 5

Full-Text Articles in Physical Sciences and Mathematics

Solvent-Free Conversion Of Alpha-Naphthaldehyde To 1-Naphthoic Acid And 1-Naphthalenemethanol: Application Of The Cannizzaro Reaction, John Esteb, Keith Gligorich, Stacy O'Reilly, Jeremy Richter Dec 2003

Solvent-Free Conversion Of Alpha-Naphthaldehyde To 1-Naphthoic Acid And 1-Naphthalenemethanol: Application Of The Cannizzaro Reaction, John Esteb, Keith Gligorich, Stacy O'Reilly, Jeremy Richter

John Esteb

The Cannizzaro reaction is routinely covered in organic textbooks, but owing to the shortage of suitable procedures for the undergraduate teaching laboratory, this reaction is seldom performed in a first-year organic chemistry class. In this experiment, powdered potassium hydroxide and α-naphthaldehyde are heated under solvent-free conditions to produce 1-naphthoic acid and 1-naphthalenemethanol in 86% and 79% yields, respectively. The solvent-free nature of this procedure greatly reduces the quantity of waste generated by students relative to the typical solvent-based method of preparation. Note:Link is to the article in a subscription database available to users affiliated with Butler University. Appropriate login information …

Go to article

Cautionary Comments (Author Response), John Esteb, Anne Wilson Dec 2003

Cautionary Comments (Author Response), John Esteb, Anne Wilson

John Esteb

Reply to concerns about a safety factor in the paper, “A Solvent-Free Oxidation of Alcohols in an Organic Laboratory."

Note:Link is to the article in a subscription database available to users affiliated with Butler University. Appropriate login information will be required for access. Users not affiliated with Butler University should contact their local librarian for assistance in locating a copy of this article.

Go to article

Simple Epoxide Formation For The Organic Laboratory Using Oxone, John Esteb Dec 2003

Simple Epoxide Formation For The Organic Laboratory Using Oxone, John Esteb

John Esteb

We present an epoxide formation experiment for a second-semester organic chemistry laboratory. This oxidation utilizes Oxone, a commercially available oxidizing agent, in the industrially relevant process of epoxide formation. The oxidant performing the oxidation is dimethyldioxirane, which is formed in situ. This experiment demonstrates a simple synthesis of an epoxide and formation of a secondary oxidizing agent.

Note:Link is to the article in a subscription database available to users affiliated with Butler University. Appropriate login information will be required for access. Users not affiliated with Butler University should contact their local librarian for assistance in locating a copy of …

Go to article

Environment-Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Triflate Catalyzed Synthesis Of Substituted 3,4-Dihydro-2h-L-Benzopyrans, Ram S. Mohan, Mai P. Nguyen, Joshua N. Arnold, Katherine E. Peterson Dec 2003

Environment-Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Triflate Catalyzed Synthesis Of Substituted 3,4-Dihydro-2h-L-Benzopyrans, Ram S. Mohan, Mai P. Nguyen, Joshua N. Arnold, Katherine E. Peterson

Ram S. Mohan

A highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed. An extension of this method to the synthesis of a pyrano [2,3,b]benzopyran has also been achieved. Bi(OTf)3.xH2O (1< x < 4) (0.1mol%) smoothly catalyzes the condensation of substituted salicylaldehydes with 2,2-dimethoxypropane to give the corresponding substituted 3,4-dihydro-2H-1-benzopyrans as a mixture of diastereomers (9:1) in moderate yields. The relative configuration of the methoxy groups in the two diastereomers was established by NOE experiments. The advantages of this method include the use of an easy to handle, inexpensive and relatively non-toxic catalyst.

Go to article

Bismuth Compounds In Organic Synthesis. Bismuth Nitrate Catalyzed Chemoselective Synthesis Of Acylals From Aromatic Aldehydes, Ram S. Mohan, David H. Aggen, Joshua N. Arnold, Patrick D. Hayes, Nathaniel J. Smoter Dec 2003

Bismuth Compounds In Organic Synthesis. Bismuth Nitrate Catalyzed Chemoselective Synthesis Of Acylals From Aromatic Aldehydes, Ram S. Mohan, David H. Aggen, Joshua N. Arnold, Patrick D. Hayes, Nathaniel J. Smoter

Ram S. Mohan

1Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 3–10 mol% Bi(NO3)3•5H2O. Ketones are not affected under the reaction conditions. The relatively non-toxic nature of the catalyst, its ease of handling, easy availability and low cost make this procedure especially attractive for large-scale synthesis.

Go to article