Application of trityl moieties in chemical processes: part I

Baghery, Saeed; Zarei, Mahmoud; Zolfigol, Mohammad Ali; Mallakpour, Shadpour; Behranvand, Vajiheh

doi:10.1007/s13738-020-01980-5

Cited by 3 publications

(4 citation statements)

References 514 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[α] D 20 +5 (c 2.32, CHCl 3 ). 1 H NMR (300 MHz, CDCl 3 ) δ 7.30− 7.20 (m, 15H), 5.04 (h,J = 6.3 Hz,1H),2H), 1.18− 1.04 (m, 2H), 1.17 (d,J = 6.3 Hz,3H),0.79 (t,J = 7.3 Hz,3H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ 173.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…The dynamic stereochemistry and residual stereoisomerism of molecular propellers were the subjects of intense studies initiated by Mislow in the early 1970s. − Then, after a nearly 20 year period of freezing activity in the field, there was renewed interest in molecular propellers associated with their increasing number of applications. One of the simplest entities showing propensity to residual stereoisomerism, namely, the triphenylmethyl group (CPh 3 , Tr, trityl), is currently used in organic synthesis as protecting devices, catalysts, , construction of molecular machines, medical chemistry, and bioimaging …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Chiral Triphenylacetic Acid Esters: Residual Stereoisomerism and Solid-State Variability of Molecular Architectures

2021

View full text Add to dashboard Cite

We have proven the usability and versatility of chiral triphenylacetic acid esters, compounds of high structural diversity, as chirality-sensing stereodynamic probes and as molecular tectons in crystal engineering. The low energy barrier to stereoisomer interconversion has been exploited to sense the chirality of an alkyl substituent in the esters. The structural information are cascaded from the permanently chiral alcohol (inducer) to the stereodynamic chromophoric probe through cooperative interactions. The ECD spectra of triphenylacetic acid esters are highly sensitive to very small structural differences in the inducer core. The tendencies to maximize the C–H···O hydrogen bonds, van der Waals interactions, and London dispersion forces determine the way of packing molecules in the crystal lattice. The phenyl embraces of trityl groups allowed, to some extent, the control of molecular organization in the crystal. However, the spectrum of possible molecular arrangements is very broad and depends on the type of substituent, the optical purity of the sample, and the presence of a second trityl group in the proximity. Racemates crystallize as the solid solution of enantiomers, where the trityl group acts as a protecting group for the stereogenic center. Therefore, the absolute configuration of the inducer is irrelevant to the packing mode of molecules in the crystal.

show abstract

Section: ■ Conclusionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chiral Triphenylacetic Acid Esters: Residual Stereoisomerism and Solid-State Variability of Molecular Architectures

2021

View full text Add to dashboard Cite

show abstract

“…TrBF 4 is a safe, commercialized, and inexpensive Lewis acid and has been extensively used in organic synthesis as a protection reagent or catalyst . However, the compound itself and its derivatives are much less employed in polymer synthesis. ,− Very recently, we found a derivative of TrBF 4 could induce a photo-controlled living cationic polymerization of methoxystyrene .…”

Section: Introductionmentioning

confidence: 99%

Living Cationic Polymerization of ε-Caprolactone Catalyzed by a Metal-free Lewis Acid of Trityl Tetrafluoroborate

Wang

Chen

et al. 2023

Macromolecules

View full text Add to dashboard Cite

Research on metal-free catalytic synthesis of polycaprolactone (PCL) is fueled by the many practical needs for biodegradable and biocompatible materials. In this regard, the pursuit of effective and economical catalysts as well as precise control over the polymerization has become the main challenge. Herein, we report a living cationic ring-opening polymerization of ε-caprolactone catalyzed by a safe, inexpensive, and metal-free Lewis acid of trityl tetrafluoroborate. The polymerization is initiated by alcohol or water, which is corroborated by the presence of initiator segments at the chain ends of PCL polymers via 1H NMR and matrix-assisted laser desorption ionization time-of-flight mass spectrometry. Kinetic experiments show that polymerization is a first-order reaction to monomers. This result, together with the predictable molar mass, narrow molar-mass dispersity, and controllable chain growth and extension, confirms the synthesis to be a living polymerization. This work expands the catalytic toolbox of PCL synthesis and represents a rare example of cationic living polymerization of ε-caprolactone catalyzed by Lewis acids.

show abstract

“…The trityl group has many applications in organic synthesis and supramolecular chemistry. Usually it acts as a protecting group for reactive functional groups or (in the ionized form) as a catalyst in chemical processes (Baghery et al, 2020;Kocienski, 2005;Nair et al, 2006). Moreover, it has been shown that the trityl group, when linked to a stereogenic centre, can act as a chiral reporter (S ´ciebura et al, 2009;S ´ciebura & Gawron ´ski, 2011).…”

Section: Introductionmentioning

confidence: 99%

Diversity of N-triphenylacetyl-L-tyrosine solvates with halogenated solvents

Czapik¹,

Kwit²

2021

Acta Crystallogr C

View full text Add to dashboard Cite

The structure of N-triphenylacetyl-L-tyrosine (C29H25NO4, L-TrCOTyr) is characterized by the presence of both donors and acceptors of classical hydrogen bonds. At the same time, the molecule contains a sterically demanding and hydrophobic trityl group capable of participating in π-electron interactions. Due to its large volume, the trityl group may favour the formation of structural voids in the crystals, which can be filled with guest molecules. In this article, we present the crystal structures of a series of N-triphenylacetyl-L-tyrosine solvates with chloroform, namely, L-TrCOTyr·CHCl3 (I) and L-TrCOTyr·1.5CHCl3 (III), and dichloromethane, namely, L-TrCOTyr·CH2Cl2 (II) and L-TrCOTyr·0.1CH2Cl2 (IV). To complement the topic, we also decided to use the racemic amide N-triphenylacetyl-DL-tyrosine (rac-TrCOTyr) and recrystallized it from a mixture of chloroform and dichloromethane. As a result, rac-TrCOTyr·1.5CHCl3 (V) was obtained. In the crystal structures, the amide molecules interact with each other via O—H...O hydrogen bonds. Noticeably, the amide N—H group does not participate in the formation of intermolecular hydrogen bonds. Channels are formed between the TrCOTyr molecules and these are filled with solvent molecules. Additionally, in the crystals of III and V, there are structural voids that are occupied by chloroform molecules. Structure analysis has shown that solvates I and II are isostructural. Upon loss of solvent, the solvates transform into the solvent-free form of TrCOTyr, as confirmed by thermogravimetric analysis, differential scanning calorimetry and powder X-ray diffraction.

show abstract

Application of trityl moieties in chemical processes: part I

Cited by 3 publications

References 514 publications

Chiral Triphenylacetic Acid Esters: Residual Stereoisomerism and Solid-State Variability of Molecular Architectures

Chiral Triphenylacetic Acid Esters: Residual Stereoisomerism and Solid-State Variability of Molecular Architectures

Living Cationic Polymerization of ε-Caprolactone Catalyzed by a Metal-free Lewis Acid of Trityl Tetrafluoroborate

Diversity of N-triphenylacetyl-L-tyrosine solvates with halogenated solvents

Contact Info

Product

Resources

About