Tetrahedron, 01 January 2000, Vol.56(1), pp.57-62
Bis-triphenylphosphonio-isophosphindolide cations 1 react with triflic acid to give C-protonated products 4 , 5 which show an enhanced reactivity to undergo addition of H 2 O or MeOH to the cyclic π-system. This reaction is the first step of the hydrolytic decomposition of the heterocycle which was monitored by NMR spectroscopic studies. No evidence for direct P-protonation or P-alkylation (which had been postulated in a previous study) was obtained. Addition of H 2 O or H 2 S to the cyclic π-system of 1 is also promoted by oxidizing agents such as I 3 − or sulfur and affords novel zwitterionic (thio)-phosphinates 11 , 13 .
Addition Reactions ; Ambiphilic Activity ; Phospholes ; Protonation ; Chemistry
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