Developments in the deprotection of thioacetals

Abstract

Dithioacetals are very important and commonly used protecting groups for carbonyl compounds. Among the advantages of their use are the ease of formation, stability under both acidic and basic conditions, and umpolung reactivity. Unfortunately, their deprotection into the corresponding carbonyls is quite often difficult and requires special conditions. Hence, numerous protocols for the dithiane deprotection have been devised. In this review, various methodologies that were developed for the hydrolysis of thioacetal protecting groups are summarised and the detailed reaction conditions are presented.

Keywords:

• Dithiane
• Thioacetal
• Dithiolane
• Deprotection
• Hydrolysis

Acknowledgements

The author wishes to express his sincere thanks to Professors P.V. Ramachandran and John B. Grutzner.

Additional information

Notes on contributors

T. E. Burghardt

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