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- W1838748049 abstract "Reaction of benzyl and ethyl allenoates with TMSX (X = I, Br, Cl) and with NH 4 SCN were investigated in MeCN, DMF, and in imidazolium ionic liquids [BMIM][NTf 2 ] and [BMIM][PF 6 ] as solvent, in the presence and absence of Selectfluor . Comparative product analysis studies demonstrate that the ability of Selectflour to promote oxidative/electrophilic dihalogenation/dithiocyanation with TMSX/NH 4 SCN (as observed previously for 1-arylallenes) is diminished in allenoates, most significantly in reactions with TMSCl, and essentially disappearing in reactions with NH 4 SCN, in favor of nucleophilic/conjugate addition. The study underscores the contrasting reactivity patterns in 1-arylallenes and allenoates toward electrophilic and nucleophilic additions in halofunctionalization with TMSX/Selectfluor and thiocyanation reactions with NH 4 SCN/Selectfluor. These competing pathways are influenced by the nature of the anion, allene structure, and the choice of solvent." @default.
- W1838748049 created "2016-06-24" @default.
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- W1838748049 date "2015-09-16" @default.
- W1838748049 modified "2023-10-12" @default.
- W1838748049 title "Reaction of allene esters with Selectfluor/TMSX (X = I, Br, Cl) and Selectfluor/NH4SCN: Competing oxidative/electrophilic dihalogenation and nucleophilic/conjugate addition" @default.
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- W1838748049 doi "https://doi.org/10.3762/bjoc.11.180" @default.
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