Mild Organic Ammonium Tribromide–Mediated Regioselective Ring Opening of Epoxides with Alcohols, Water, Acetic Anhydride, and Amines Under Solvent-Free Reaction Conditions

Abstract

Organic ammonium tribromide (OATB), N-methylpyrrolidine-2-one hydrotribromide (MPHT) was found to be an efficient catalyst for the regioselective ring opening of epoxides with various nucleophiles under solvent free conditions. This procedure occurs under neutral and mild reaction conditions with out adding any additive and afforded high yields of products.

Keywords:

• Metal free
• MPHT
• regioselective synthesis
• ring opening
• solid bromine

ACKNOWLEDGMENTS

We are grateful to the director, Indian Institute of Petroleum, for his kind permission to publish these results. S. L. J. and S. S. are thankful to the Council of Scientific and Industrial Research New Delhi, for the award of research fellowships.

Notes

^a Reaction conditions: epoxide (1 mmol), MPHT (1.2 mmol), acetonitrile (3 ml); reaction time 15–20 min at room temperature.

^b Isolated yields.

^a Reaction conditions: Epoxide (1 mmol), nucleophile (2 mmol), and MPHT (10 mol%) at room temperature.

^b Isolated yields.

^a Reaction conditions: Epoxide (1 mmol), amine (2.0 mmol), MPHT and (10 mol%) at room temperature.

^b Isolated yields.