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Observation of intermediates in reaction of non-stabilized phosphonium ylide containing phosphaboratatriptycene skeleton with PhCHO

Abstract The signals of intermediates in the reaction of non-stabilized phosphonium ylide containing a phosphaboratatriptycene skeleton with PhCHO were observed as broad singlets at around −4.56 ∼ −5.77 ppm between −50 °C and −10 °C by variable temperature (VT) 31P{1H} NMR spectroscopy. The signals assignable to the same intermediates were also observed from −90 °C to −10 °C in the deprotonation of the diastereomeric mixture of β-hydroxyalkylphosphonium salts containing a phosphaboratatriptycene skeleton with TMS2NNa by VT-31P{1H} NMR spectroscopy. The results strongly suggested that the observed phosphorus signals were not assigned to 1,2-oxaphosphetanes but betaine intermediates because the signals due to 1,2-oxaphosphetanes containing phosphaheteratriptycene skeletons with Group 14 and 15 elements were observed around −55.7 ∼ −82.8 ppm except for Bi. Graphical Abstract