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A Simple and Practical Synthetic Protocol for Acetalisation, Thioacetalisation and Transthioacetalisation of Carbonyl Compounds under Solvent‐Free Conditions
Author(s) -
Khan Abu T.,
Mondal Ejabul,
Ghosh Subrata,
Islam Samimul
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300685
Subject(s) - chemistry , sulfonium , catalysis , solvent , organic chemistry , ring (chemistry) , bromide , double bond , salt (chemistry)
A wide variety of carbonyl compounds can be converted smoothly to the corresponding acetals on treatment with alcohols or diols and triethyl orthoformate in the presence of a catalytic amount of (bromodimethyl)sulfonium bromide at room temperature. Similarly, various carbonyl compounds can be transformed into the corresponding dithioacetals on reaction with thiol or dithiols at room temperature by employing the same catalyst without any solvent. Moreover, O,O‐acetals can also be converted into the corresponding dithioacetals under identical conditions. Some of the major advantages are mild reaction conditions, a high degree of efficiency, compatibilty with other protecting groups and the lack of solvents, particularly for thioacetalisation. In addition, no brominations occur at the double bond or α to the keto position or even in the aromatic ring under these experimental conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)