Efficient and Chemoselective Conversion of Carbonyl Compounds to 1,3-Dioxanes Catalyzed with N-Bromosuccinimide under Almost Neutral Reaction Conditions

Babak Karimi*, G. Reza Ebrahimian and Hassan Seradj

*Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P.O. Box 45195-159, Gava Zang, Zanjan, Iran, Email: karimiiasbs.ac.ir

B. Karimi, G. R. Ebrahimian, H. Seradj, Org. Lett., 1999, 1, 1737-1739.

DOI: 10.1021/ol9909987

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Abstract

Carbonyl compounds were converted to the corresponding 1,3-dioxanes in the presence of ethyl orthoformate, 1,3-propanediol, and a catalytic amount of NBS via an in situ acetal exchange process. The reaction tolerates acid-sensitive groups such as THP ethers and TBDMS ethers.

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Iodine-Catalyzed, Efficient and Mild Procedure for Highly Chemoselective Acetalization of Carbonyl Compounds under Neutral Aprotic Conditions

B. Karimi, B. Golshani, Synthesis, 2002, 784-788.

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Key Words

1,3-Dioxanes

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ID: J54-Y1999