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1,3-Dibromo-5,5-dimethylhydantoin or N-bromosuccinimide as efficient reagents for chemoselective deprotection of 1,1-diacetates under solvent-free conditions

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Abstract

A simple and efficient method is reported for rapid chemoselective transformation of 1,1-diacetates to the parent aldehydes using 1,3-dibromo-5,5-dimethylhydantoin or N-bromosuccinimide in the presence of wet SiO2 (50%, w/w) as solid support under solvent-free conditions at room temperature. This procedure has valuable advantages, for example short reaction times, simple work-up, high yields of products, absence of solvent, and use of commercially available and non-toxic reagents.

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Acknowledgments

The authors wish to thank the University of Tarbiat Moallem Sabzevar and Bu-Ali Sina University in Hamadan for financial support to carry out this research. We also thank Mrs Neda Rahiminezhad for her assistance.

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Authors and Affiliations

  1. Department of Chemistry, Sabzevar Tarbiat Moallem University, Sabzevar, Iran

    Behrooz Maleki, Seyedeh Fatemeh Hojati, Mostafa Gholizadeh, Hafezeh Salehabadi & Mona Khodaverdian Moghadam

  2. Department of Chemistry, Bu-Ali Sina University, Hamadan, Iran

    Davood Azarifar & Ramin Ghorbani-vaghei

  3. Department of Chemistry, Payame Noor University, Songhor, Kermanshah, Iran

    Hojat Veisi

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  1. Behrooz Maleki
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  2. Davood Azarifar
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  5. Seyedeh Fatemeh Hojati
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  8. Mona Khodaverdian Moghadam
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Correspondence to Behrooz Maleki.

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Maleki, B., Azarifar, D., Ghorbani-vaghei, R. et al. 1,3-Dibromo-5,5-dimethylhydantoin or N-bromosuccinimide as efficient reagents for chemoselective deprotection of 1,1-diacetates under solvent-free conditions. Monatsh Chem 140, 1485–1488 (2009). https://doi.org/10.1007/s00706-009-0212-9

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  • DOI: https://doi.org/10.1007/s00706-009-0212-9

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