Synthesis of the borneol isomer isoborneol via reduction of camphor.

In principle, the reduction of camphor can give two diastereomeric alcohols,corresponding to reaction of borohydride at the two faces of the C=O bond. Reaction at thetop ("exo") face regenerates the original starting material, borneol. Reactionat the bottom ("endo") face yields the other diastereomer, isoborneol:

Synthesis of Camphor by the Oxidation of Borneol | …

Oxidation of Borneol to Camphor Using Oxone and …

X. Jones Reaction: The Oxidation of Borneol to Camphor

Ceacero-Vega, A. A.; Ballesteros, B.; Bejan, I.; Barnes, I.; Jiménez, E.; Albaladejo, J. Kinetics and Mechanisms of the Tropospheric Reactions of Menthol, Borneol, Fenchol, Camphor, and Fenchone with Hydroxyl Radicals (OH) and Chlorine Atoms (Cl). J. Phys. Chem. A 2012, 116 (16), 4097-4107. Rafiński, Z.; Kozakiewicz, A. Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1R)-Camphor-Derived N-Heterocyclic Carbenes. J. Org. Chem. 2015, 80 (15), 7468-7476. McLain, K. A.; Miller, K. A.; Collins, W. R. Introducing Organic Chemistry Students to Natural Product Isolation Using Steam Distillation and Liquid Phase Extraction of Thymol, Camphor, and Citral, Monoterpenes Sharing a Unified Biosynthetic Precursor. J. Chem. Educ. 2015, 92 (7), 1226-1228.

Borneol, Camphor, and Isoborneol

Inspection of a molecular model of camphor will reveal that the exo face isconsiderably more sterically hindered than the endo face, due to the presence of one ofthe methyl groups. Since "endo-attack" of borohydride avoids thissteric interaction, we might predict that it should proceed faster than exo-attack,leading to stereoselective reduction. The use of steric effects to control reactivity inthis way is termed steric approach control. The extent to which we are successfulin controlling the stereoselectivity of the reduction will be gauged by determining therelative yields of borneol and isoborneol using gas chromatography.

Denisse CuarterosLaboratory 4B: Green Oxidation of Borneol to Camphor Short response 1
Oxidation of Borneol to Camphor 13 Mar 2015

BORNEOL OXIDATION: SYNTHESIS OF CAMPHOR - …

Hypochlorite Oxidation of endo-Borneol to Camphor …

BORNEOL OXIDATION: SYNTHESIS OF CAMPHOR a