Oxidation of Borneol to Camphor Using Oxone and Catalytic Sodium Chloride: A Green Experiment for the Undergraduate Organic Chemistry Laboratory

Abstract

ACKNOWLEDGMENTWe thank the students and teaching assistants in the 2311 Organic Chemistry Laboratory course spring and summer semesters of 2010 for their participation in the development of this new laboratory experiment. We also thank Letitia J. Yao for her assistance with the 1 H NMR data and Patrick Schildt and the organic chemistry stockroom personnel for their patience and support in trial runs of a new experiment.

Sequential Silver‐Catalyzed Oxidative Cyclization Reactions of Unprotected 2‐Alkynylanilines to Anthranils

“…Conversely, only 1‐(benzo[ c ]isoxazol‐3‐yl)‐2‐phenylethane‐1,2‐dione ( 4cj ) was isolated from 3‐(2‐aminophenyl)‐1‐phenylprop‐2‐yn‐1‐ol ( 3cj ; Scheme ). Benzylic alcohols are more prone to oxidation by Oxone . Therefore, the further oxidative cleavage of the 1,2‐dione 4cj that occurs under our reactions conditions limits its synthetic utility.…”

Re-casting traditional organic experiments into green guided-inquiry based experiments: student perceptions

“…A collaboration of Organic chemistry educators presented a comprehensive summary of experimental and theoretical applications of green chemistry in Organic experiments in a publication edited by Dicks (2). A small subset of articles shows a variety of greener principles or methods are used in these new or revised experiments such as microwave irradiation, solvent-free conditions, and safer reagents or solvents (3)(4)(5)(6)(7)(8)(9). Montes et al (3) have developed a greener synthesis of aspirin using microwave irradiation.…”

“…Lang et al used Oxone for a greener oxidation of borneol, in which the product would be used in a research group. The authors surveyed their students about their opinions on the experiment and found that they valued green chemistry in their curriculum (9). Other chemical disciplines are seeing greener methods, though many are published without specifically being associated with green chemistry or sustainability (10).…”

Polyethylene Glycols as Efficient Catalysts for the Oxidation of Bicyclic Monoterpenes by Ceric Ammonium Nitrate in Acetonitrile under Acid‐Free Conditions: Kinetic and Mechanistic Approach

“…Isobornyl ethanoate upon hydrolysis affords isoborneol, which upon oxidation gives camphor. On the other hand, oxidation of borneol also gives camphor . Camphor upon oxidation is known to form camphoronic acid .…”

“…Camphor upon oxidation is known to form camphoronic acid . During the past few decades, single‐electron transfer (SET) oxidation has received considerable attention as a means to promote bond‐forming reactions in organic synthesis . Oxidation of an organic substrate by a SET reagent generally proceeds through a radical or radical–ion followed by the reduction of oxidizing reagent .…”