Studies on the [2+3] cycloaddition reaction of nitrile oxides to abietic acid esters

Gucma, Mirosław; Golebiewski, W. Marek; Żelechowski, Krzysztof; Krawczyk, Maria

doi:10.2298/jsc180517018g

Cited by 1 publication

(2 citation statements)

References 20 publications

(26 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Gołębiewski et al described high regio- and site-selectivity of the [2 + 3] cycloaddition of p -XC 6 H 4 CNO to selected abietates— Scheme 268 [ 282 ].…”

Section: Syntheses Of Substituted 2-isoxazolines Via 13-dp Cycloaddit...mentioning

confidence: 99%

See 1 more Smart Citation

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

et al. 2023

View full text Add to dashboard Cite

The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and with alkene metathesis (AM) in the syntheses of trisubstituted isoxazolines. Allyl compounds of the type QCH2CH=CH2 (Q = ArO, ArS, Ar, and others) play the role of dipolarophile precursors in the combinations of DPC mentioned, DBM and AM. Mechanistic aspects of cycloadditions, i.e., concerted or stepwise reaction mechanism and their regio- and stereoselectivity are also discussed from experimental and theoretical points of view. Side reactions accompanying cycloaddition, especially nitrile oxide dimerization, are considered. 2-Isoxazoline applications in organic synthesis and their biological activity, broad utility in medicine, agriculture, and other fields were also raised. Some remaining challenges in the field of 1,3-DP cycloaddition in the syntheses of isoxazolines are finally discussed.

show abstract

“…Gołębiewski et al described high regio- and site-selectivity of the [2 + 3] cycloaddition of p -XC 6 H 4 CNO to selected abietates— Scheme 268 [ 282 ].…”

Section: Syntheses Of Substituted 2-isoxazolines Via 13-dp Cycloaddit...mentioning

confidence: 99%

“… Syntheses of 3,4,5,5-trisubstituted 2-isoxazolines from selected abietates [ 282 ]. R 1 , R 2 = Me, CF 3 ; Me, i -Pr; Ph, CF 3 ; Bn, CF 3 ; a = CH 2 Cl 2 , rt, overnight, up to 15% yield.…”

Section: Figures and Schemesmentioning

confidence: 99%

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

et al. 2023

View full text Add to dashboard Cite

show abstract

Studies on the [2+3] cycloaddition reaction of nitrile oxides to abietic acid esters

Abstract: Dipolar cycloadditions of aromatic nitrile oxides to abietic acid esters were investigated. The reactions showed complete site selectivity and regioselectivity, while the stereoselectivity depended on the structures of the dipolarophiles.

Cited by 1 publication

References 20 publications

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

Contact Info

Product

Resources

About