Triphenylcarbenium Tetrafluoroborate

Jung, Michael E.; Lagoutte, Roman; Jahn, Ullrich

doi:10.1002/047084289x.rt362.pub2

Encyclopedia of Reagents for Organic Synthesis 2011

DOI: 10.1002/047084289x.rt362.pub2

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Triphenylcarbenium Tetrafluoroborate

Michael E. Jung¹,

Roman Lagoutte²,

Ullrich Jahn³

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Cited by 2 publications

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“…We thus decided to try different Lewis acids with the goal of reducing the extent of di- tert -butylsilanediol formation. While triflate salts of zinc, indium, and ytterbium (Table , entries 7–9, respectively) did not help reaction performance, with 10 mol % of the unusual Lewis acid triphenylcarbenium tetrafluoroborate (Table , entry 10), product formation was excellent with no discernible starting material fragmentation.…”

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Ring Opening of Epoxides by Pendant Silanols

2022

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We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph 3 C + BF 4 − or BINOLphosphoric acid. Silanol epoxides derived from trans-allylic alcohols, cis-allylic alcohols, trans-homoallylic alcohols, and cishomoallylic alcohols were all compatible and gave products from either endo-or exo-ring opening. With silanol epoxides derived from 4-alkenyl silanols, an unusual rearrangement to tetrahydrofuran products was observed. The utility of this methodology was demonstrated in a short preparation of protected D-arabitol.

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Ring Opening of Epoxides by Pendant Silanols

2022

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Optical nature of non‐substituted triphenylmethyl cation: Crystalline state emission, thermochromism, and phosphorescence

et al. 2021

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Since the discovery of the triphenylmethyl (trityl) cation 120 years ago, a variety of aromatic cations having various colors and luminescence properties have been rigorously studied. Many, differently substituted trityl cations have been synthesized, and their optical properties have been elucidated. However, the optical properties of the parent, non-substituted and highly reactive trityl cation, which was observed to be very weakly luminescent, have not been subjected to detailed investigation. In the effort described herein, we explored the optical nature of non-substituted trityl hexafluorophosphate (PF 6 ) in the crystalline state. Trityl PF 6 was found to exist as two crystal polymorphs including a yellow (Y) and an orange (O) form. Moreover, we observed that these crystalline forms display crystalline-state emission with different colors. The results of X-ray crystallographic analysis showed that the two polymorphs have totally different molecular packing arrangements. Furthermore, an investigation of their optical properties revealed that the O-crystal undergoes a distinct color change to yellow upon cooling as a consequence of a change in the nature of the charge transfer interaction between the cation and PF 6 anion, and that both the Yand O-crystal exhibit phosphorescence.

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Triphenylcarbenium Tetrafluoroborate

Cited by 2 publications

References 202 publications

Ring Opening of Epoxides by Pendant Silanols

Ring Opening of Epoxides by Pendant Silanols

Optical nature of non‐substituted triphenylmethyl cation: Crystalline state emission, thermochromism, and phosphorescence

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