Silica Gel-Supported Polyphosphoric Acid (PPA/SiO2) as an Efficient and Reusable Catalyst for Conversion of Carbonyl Compounds into Oxathioacetals and Dithioacetals

Tadashi Aoyama; Toshio Takido; Mitsuo Kodomari

doi:10.1055/s-2004-832812

LETTER

Silica Gel-Supported Polyphosphoric Acid (PPA/SiO₂) as an Efficient and Reusable Catalyst for Conversion of Carbonyl Compounds into Oxathioacetals and Dithioacetals

Tadashi Aoyama*^a, Toshio Takido^a, Mitsuo Kodomari^b
^a Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
^b Department of Applied Chemistry, Shibaura Institute of Technology, Shibaura, Minato-ku, Tokyo 108-8548, Japan
Fax: +81(3)32590818; e-Mail: aoyama@chem.cst.nihon-u.ac.jp;

Abstract

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Abstract

A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals by using polyphosphoric acid supported on silica gel (PPA/SiO₂) as an acid catalyst have been developed. PPA/SiO₂ is easily recovered from the reaction mixture and reused without a decrease in catalytic activity.

Key words

oxathioacetals - dithioacetals - protecting groups - polyphsphoric acid - silica gel

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References

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The Preparation of PPA/SiO ₂ : PPA (2.1 g) was charged in the round-bottom flask, and CHCl₃ (100 mL) was added. After the mixture was stirred at 50 ºC for 1 h, SiO₂ [Wakogel C-200 (Wako Pure Chemical Ind. Ltd.), 4.9 g] was added to the solution, and the mixture was stirred for another 1 h. The CHCl₃ was removed with rotary evaporator and the resulting solid was dried in vacuo at r.t. for 3 h.

Used PPA/SiO₂ was regenerated as follows: PPA/SiO₂ was recovered by filtration from the reaction mixture, and then it was put in the 50 mL round-bottom flask and dried in vacuo at 100 °C for 2 h.