Beilstein J. Org. Chem.2023,19, 1460–1470, doi:10.3762/bjoc.19.105
; indanones; trichloromethylgroup; triflic acid; Introduction
Superelectrophilic activation of organic compounds under the action of strong Brønsted and Lewis acids is an effective method for the synthesis of various carbocycles and heterocycles, and polyfunctional compounds (see books [1][2] and reviews [3
form of the starting compound [Cl3CCH=CHC(=OH+)Me]. The presence of two strong electron-withdrawing substituents, the trichloromethylgroup (CCl3) and a protonated carbonyl (C(OH+)Me), at the carbon–carbon double bond makes this O-protonated species electrophilic enough to react with arenes (Scheme 1a
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Graphical Abstract
Scheme 1:
Generation of O-protonated and O,C-diprotonated species from substituted conjugated enones under su...
Beilstein J. Org. Chem.2021,17, 404–409, doi:10.3762/bjoc.17.36
trifluoromethyl to a trichloromethylgroup with AlCl3 has been previously reported [30][31][32], investigations into the analogous transformation of aliphatic CF3 groups has been limited to adamantly-trifluoromethyl moieties [33][34].
An NMR analysis of the crude product mixture obtained using our original
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Graphical Abstract
Figure 1:
Examples of biologically active 1,1-dichloro-1-alkenes.