An Improved Process for the Preparation of an ?,?-Difluorosulfonylisoxazoline Herbicide

Belie, Chantal; Boehmer, Jutta; Clarke, Eric D.; Dalencon, Anne J.; Dallimore, Jonathan W. P.; Diggelmann, Martin; Qacemi, Myriem El; Ingram, Katharine; Knee, Andy; Kozakiewicz, Tony; Longstaff, Adrian; McCormack, Derek P.; McLachlan, Matthew M. W.; Mulholland, Nick; Plant, Andrew; Williams, John

doi:10.2533/chimia.2014.442

Cited by 1 publication

(1 citation statement)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, even if MeOH seems to have an essential role in the mechanism depicted in Scheme 11, the reaction has been carried out also in other solvents such as DMSO and DMF [103,77] . Interestingly, 3‐Chloro‐Δ 2 ‐isoxazolines are susceptible to addition‐elimination also in the presence of thiourea [106] or NaSCN [107] …”

Section: Reactivity Of 3‐bromo‐45‐dihydroisoxazolesmentioning

confidence: 99%

Synthesis and Reactivity of 3‐Halo‐4,5‐dihydroisoxazoles: An Overview

Zana

Galbiati

2021

ChemistrySelect

View full text Add to dashboard Cite

The 3‐halo‐4,5‐dihydroisoxazole moiety is an interesting emerging feature in medicinal and organic chemistry fields. The properties of this nucleus are intimately correlated with the nature of the halogen substituent, ranging from inertness to instability. In between, the 3‐bromo‐Δ2‐isoxazoline scaffold stands out as a handleable and easily affordable electrophilic warhead, able to react with nucleophilic active sites of different enzymes, determining inhibitory effects. However, the importance of 3‐bromo‐Δ2‐isoxazolines does not rely only upon their biological activity. In fact, they are valuable synthetic intermediates, presenting a peculiar reactivity spectrum that allows access to useful chemical functions, ranging from variously decorated dihydroisoxazoles to β‐hydroxynitriles, β‐hydroxyesters, and γ‐hydroxyamines. The synthesis of 3‐bromo‐Δ2‐isoxazolines is predominantly based on the 1,3‐dipolar cycloaddition, a pericyclic reaction accompanied by a remarkable regio‐ and stereo‐selectivity. Thus, this intermediate lends itself especially well to the production of complex molecules with regio‐ and stereo‐chemical requirements.

show abstract

Section: Reactivity Of 3‐bromo‐45‐dihydroisoxazolesmentioning

confidence: 99%