Chemoselective and Chemospecific Protection and Deprotection of a Carbonyl Group Using Polystyrene Divinylbenzene Sulfonic Acid

Abstract

Chemospecific protection of one carbonyl group of two identical carbonyls of 2,2-dialkyl-1,3-cyclohexanedione and chemoselective protection of aliphatic or aromatic carbonyls in the presence of conjugated carbonyl compounds using cross-linked polystyrene divinyl benzene sulfonic acid (SPS) as a heterogeneous catalyst has been demonstrated.

Keywords:

• 2,2-Dialkyl-1,3-cyclohexanedione
• chemoselectivity
• chemospecificity
• polystyrene divinyl benzene sulfonic acid

ACKNOWLEDGMENT

We thank Dr. Vijayaraghavan, director of the Defence Research and Development Establishment, Gwalior, for his keen interest and encouragement.

Notes

Note. All the products were compared with authentic sample and gave satisfactory IR, NMR, and MS data.

^a Isolated yields. In the case of dione, yield is only of monoprotected carbonyls.

^a Yield is only of monoprotected product.

^b GC yield.

Note. All the products were compared with authentic samples and gave satisfactory IR, NMR, and MS data.

^a Isolated yield.