Tetrahedron p. 3425 - 3430 (1984)
Update date:2022-08-02
Topics:
Patonay, Tamas
Litkei, Gyoergy
Bognar, Rezsoe
The action of either cyanate or acetate ions on trans-3-mesyloxyflavanones 1 led to the formation of flavones 2 and aurones while the reaction with the respective S-nucleophiles (thiocyanate and thioacetate ions) resulted in cis- and trans-3-thiocyanato- and 3-acetylthioflavanones (6 and 11).The participation of the concurrent nucleophilic substitution, β-elimination and elimination with ring-contraction is dependent on the "hard-soft" character of the nucleophile and the increase of the "soft" character favours the displacement.
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Doi:10.1080/15421406.2012.676834
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(1984)Doi:10.1039/c9ra04311j
(2019)