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Substituent effects on stereoselectivity of dihalocarbene reactions with cyclohexadiene and on the reactivity of bis-dihalocyclopropanes in electrophilic nitrations en route to pyrimidine N-oxides.

Organic & biomolecular chemistry

Sedenkova KN, Averina EB, Grishin YK, Kolodyazhnaya JV, Rybakov VB, Kuznetsova TS, Hughes A, Gomes GDP, Alabugin IV, Zefirov NS.
PMID: 29095467
Org Biomol Chem. 2017 Nov 15;15(44):9433-9441. doi: 10.1039/c7ob02463k.

Tricyclic bis-adducts of cyclohexa-1,4-diene with bromofluorocarbene and non-symmetric adducts with both bromofluoro- and dichlorocarbenes were synthesised selectively. The treatment of the bis-adducts with nitrating reagents in acetonitrile affords the products of heterocyclization of a sole dihalogenocyclopropane into 4-fluoropyrimidine N-oxide....

Showing 61 to 61 of 61 entries