Simple, Mild and Efficient Thioacetalization and Transthioacetalization of Carbonyl Compounds and Deprotection of Thioacetals: Unique Role of Thiols in the Selectivity of Thioacetalization [1]

Abstract

Silica supported sodium hydrogen sulfate (NaHSO₄·SiO₂) has been employed for efficient thioacetalization and transthioacetalization of carbonyl compounds in CH₂Cl₂ at room temperature. Selectivity of thioacetalization was dependent on the thiols used for the conversion. The same catalyst was also found to be effective for deprotection of thioacetals in CH₂Cl₂-H₂O at room temperature.

Keywords

carbonyl compounds - thioacetalization - transthioacetalization - deprotection of thioacetals - NaHSO₄·SiO₂ - selectivity

1

Part 39 in the series ‘Studies on novel synthetic methodologies’; IICT Communication No. 041106.

References

• 2a Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   2nd ed.:  Wiley; New York: 1991.  p.178-207  
• 2b Kocienski PJ. Protecting Groups   Thieme; Stuttgart: 1994.  p.156-170  
• 3a Corey EJ. Seebach D. Angew Chem. Int. Ed. Engl.  1965,  4:  1075 
• 3b Corey EJ. Seebach D. J. Org. Chem.  1966,  31:  4097 
• 4a Colvin EW. Raphael RA. Roberts JS. J. Chem. Soc., Chem. Commun.  1971,  858 
• 4b Corey EJ. Erickson BW. J. Org. Chem.  1971,  36:  3553 
• 4c Ho TL. Ho HC. Wong CM. J. Chem. Soc., Chem. Commun.  1972,  791 
• 4d Dishi T. Kamemoto K. Ban Y. Tetrahedron Lett.  1972,  13:  1085 
• 4e Ellision RA. Lukenbach ER. Chiu CW. Tetrahedron Lett.  1975,  499 
• 4f Schmittel M. Levis M. Synlett  1996,  315 
• 4g Hirano A. Ukawar K. Yakabe S. Clark JH. Morimoto T. Synthesis  1997,  858 
• 5a Dijerassi C. Gorman M. J. Am. Chem. Soc.  1953,  75:  3704 
• 5b Fieser LF. J. Am. Chem. Soc.  1954,  76:  1945 
• 5c Olah GA. Narang SC. Meider D. Salem GF. Synthesis  1981,  282 
• 5d Corey EJ. Shimoji K. Tetrahedron Lett.  1983,  24:  169 
• 5e Page PCB. Prodger JC. Westwood D. Tetrahedron  1993,  49:  10355 
• 5f Tateiwa J. Horiuchi H. Uemura S. J. Org. Chem.  1995,  60:  4039 
• 5g Firouzabadi H. Iranpoor N. Karimi B. Synthesis  1999,  58 
• 5h Yadav JS. Reddy BVS. Pandey SK. Synlett  2001,  238 
• 5i Kamal A. Choudhan G. Tetrahedron Lett.  2003,  44:  3337 
• 5j Yadav JS. Reddy BVS. Kondaji G. Chem. Lett.  2003,  32:  672 
• 6a Mahender G. Ramu R. Ramesh C. Das B. Chem. Lett.  2003,  32:  734 
• 6b Ramesh C. Banerjee J. Pal R. Das B. Adv. Synth. Catal.  2003,  557 
• 6c Ramesh C. Ravindranath N. Das B. J. Org. Chem.  2003,  68:  7101 
• 7 Breton GW. J. Org. Chem.  1997,  62:  8952 

1

Part 39 in the series ‘Studies on novel synthetic methodologies’; IICT Communication No. 041106.