Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3\u2009+\u20092] cycloaddition

Barbara Mirosław,Agnieszka Łapczuk-Krygier,Oleg M Demchuk,Dmytro Babyuk,Radomir Jasiński,Agnieszka Kącka-Zych

doi:10.1007/s00706-018-2227-6

Abstract

5-(Nitromethyl)-3-phenyl-4,5-dihydroisoxazole was obtained as a product of a high-yielding [3 + 2] cycloaddition reaction of in situ-generated benzonitrile N-oxide and 3-nitroprop-1-ene. For the first time, the regiochemistry of this reaction was unambiguously proven by X-ray structural analysis. The quantum-chemical calculation performed at the M06-2X/6-31G(d) (PCM) theoretical level affords a basis for explaining the course of reaction as well as the nature of transition states. Next, further DFT calculations together with spectral data shed light on structural aspects of the product.Graphical abstract

Highlights

5-(Nitromethyl)-3-phenyl-4,5-dihydroisoxazole was obtained as a product of a high-yielding [3 ? 2] cycloaddition reaction of in situ-generated benzonitrile N-oxide and 3-nitroprop-1-ene
The quantum-chemical calculation performed at the M06-2X/6-31G(d) (PCM) theoretical level affords a basis for explaining the course of reaction as well as the nature of transition states
It was found that the structure of 5-(nitromethyl)-3-phenyl-4,5-dihydroisoxazole should be assigned to the product

Summary

Introduction

5-(Nitromethyl)-3-phenyl-4,5-dihydroisoxazole was obtained as a product of a high-yielding [3 ? 2] cycloaddition reaction of in situ-generated benzonitrile N-oxide and 3-nitroprop-1-ene. Abstract 5-(Nitromethyl)-3-phenyl-4,5-dihydroisoxazole was obtained as a product of a high-yielding [3 ? 2] cycloaddition reaction of in situ-generated benzonitrile N-oxide and 3-nitroprop-1-ene.

Results

Conclusion