Deprotection Chemistry Mediated by ZrOCl₂ · 8H₂O: An Efficient, Mild, and Green Method for the Conversion of Oximes to Carbonyl Compounds in Aqueous Acetone

Abstract

Less-toxic, moisture-stable, inexpensive, and ecofriendly zirconium oxychloride octahydrate (ZrOCl₂ · 8H₂O) in aqueous acetone (1:1) mediates the conversion of oximes to carbonyl compounds in moderate to good yields. This green methodology is applicable to both aldoximes and ketoximes with tolerance to >C˭C<, -NO₂, -OH, and -Cl groups. The reaction and workup are simple.

Keywords:

• Carbonyl compounds
• deprotection
• green
• protection
• zirconium oxychloride octahydrate

ACKNOWLEDGMENTS

LNS and AJT are grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for financial support. SD thanks Tezpur University for the institutional fellowship. The support to record NMR spectra at the Indian Institute of Technology (IIT), Guwahati, is gratefully acknowledged.

Notes

^a Oximes 1 were synthesized according to the standard procedure and characterized by comparison of their reported spectroscopic and physical data.

^b Isolated yield.

^c All compounds gave satisfactory IR, ¹H NMR, and ¹³C NMR spectroscopic data, and finally their meeting and boiling points were compared with those of authentic samples.

^a Oximes 3 were synthesized according to the standard procedure and characterized by comparison of their reported spectroscopic and physical data.

^b Isolated yield.

^c All compounds gave satisfactory IR, ¹H NMR, and ¹³C NMR spectroscopic data, and finally their melting and boiling points were compared with those of authentic samples.