Silicasulfuric Acid/NaNO₃ as a New Reagent for the Deprotection of S,S-Acetals under Mild Conditions

Abstract

An efficient, mild and chemoselective method for the deprotection of S,S-acetal compounds to their corresponding car­bonyl compounds using silicasulfuric acid/NaNO₃ is reported.

Key word

silicasulfuric acid - sodium nitrate - deprotection - S,S-ace­tal

References

• 1 Greene TW. Protective Groups in Organic Synthesis   Wiley; New York: 1981. 
• 2 Kunz H. Waldmann H. In Comprehensive Organic Synthesis   Vol. 6:  Trost BM. Fleming I. Pergamon; New York: 1991.  p.677-681  
• 3 Corey EJ. Seebach D. J. Org. Chem.  1966,  31:  4097 
• 4 Mori Y. Kohchi Y. Suzuki M. J. Org. Chem.  1991,  56:  631 
• 5 Hajipour AR. Khoee S. Ruoho AE. Org. Prep. Proced. Int.  2003,  35:  527 
• 6 Kamal A. Reddy PSMM. Reddy R. Tetrahedron Lett.  2003,  44:  2857 
• 7a Hajipour AR. Mirjalili BF. Zarei A. Khazdooz L. Ruoho AE. Tetrahedron Lett.  2004,  45:  6607 
• 7b Zolfigol MA. Tetrahedron  2001,  57:  9509 
• 8a Fuji K. Ichikawa K. Fujita E. Tetrahedron Lett.  1978,  19:  3561 
• 8b Zolfigol MA. Mirjalili F. Bamoniri A. Karimi Zarchi MA. Zarei A. Khazdooz L. Noei J. Bull. Korean Chem. Soc.  2004,  25:  1414