Beilstein J. Org. Chem.2019,15, 1491–1504, doi:10.3762/bjoc.15.151
=)P–CR=C=CMe2, X = Cl, OMe, NR2, or SAr] undergo intramolecular cyclization into the corresponding 1,2-oxaphospholiumions in the Brønsted superacid TfOH. These cations have been thoroughly studied by means of NMR spectroscopy. The hydrolysis of superacidic solutions of these species afforded cyclic
calculations. Hydrolysis of these species resulted in the formation of phosphoryl-substituted allyl alcohols and 1,3-butadienes. A strong coordination of the oxygen of the P=O group with AlCl3 prevented the formation of cyclic 1,2-oxaphospholiumions and played a crucial role in the different reactivity of
; oxaphospholiumions; phosphorylallenes; phosphoryl group; triflic acid; Introduction
Electrophilic reactions of allenes have been intensely explored in organic synthesis [1][2][3]. In particular, reports on electrophilic activation of phosphorylallenes are numerous [4][5][6][7][8][9][10]. Miscellaneous