Rearrangements of the Radical Cations of 3-Aryl-5-fluoroisoxazoles: Further Evidence for Existence of Benzocyclopropenyl Cation.

Bondarenko, Oksana B; Komarov, Arseniy I; Nikolaeva, Svetlana N; Holt, Tina; Kutateladze, Andrei G; Gloriozov, Igor P

Bondarenko, Oksana B; Komarov, Arseniy I; Nikolaeva, Svetlana N; Holt, Tina; Kutateladze, Andrei G; Gloriozov, Igor P.

Affiliation

Bondarenko OB; Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation.
Komarov AI; Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation.
Nikolaeva SN; Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation.
Holt T; Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80208, United States.
Kutateladze AG; Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80208, United States.
Gloriozov IP; Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation.

J Am Soc Mass Spectrom ; 34(11): 2547-2555, 2023 Nov 01.

Article de En | MEDLINE | ID: mdl-37812762

ABSTRACT

ABSTRACT

The fragmentation reaction of the radical cations of 3-aryl-5-fluoroisoxazoles formed via EI-MS is described. A new rearrangement accompanied by fluorine atom migration is discovered. A mechanistic rationale for the rearrangement supporting the existence of a fluorinated benzocyclopropenyl cation was proposed based on the experimental data and quantum chemical calculations.

Mots clés

3-aryl-5-fluoroisoxazoles; DFT calculations; EI-MS fragmentation; F atom migration/rearrangement; fluorinated benzocyclopropenyl cation

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Texte intégral: 1 Collection: 01-internacional Base de données: MEDLINE Langue: En Journal: J Am Soc Mass Spectrom Année: 2023 Type de document: Article