The Journal of organic chemistry

2, 2, 6, 6-Tetramethylpiperidine-Catalyzed, Ortho-selective Chlorination of Phenols by Sulfuryl Chloride

NI Saper, BB Snider

Index: Saper, Noam I.; Snider, Barry B. Journal of Organic Chemistry, 2014 , vol. 79, # 2 p. 809 - 813

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Citation Number: 7

Abstract

2, 2, 6, 6-Tetramethylpiperidine (TMP)-catalyzed (1–10%) chlorinations of phenols by SO2Cl2 in aromatic solvents are more ortho selective than with primary and less hindered secondary amine catalysts. Ortho-selective chlorination is successful even with electron deficient phenols such as 2-hydroxybenzaldehyde and 2′-hydroxyacetophenone. Notably, ortho selectivity increases with the reaction temperature. On the other hand, ...