scholarly journals Bifunctional sulfur-silicon podands as new nucleophilic ionophores in acyl transfer reactions. Influence of monovalent cations on the reaction kinetics

2006 ◽  
Vol 4 (2) ◽  
Author(s):  
Bogusława ŁLęska ◽  
Grzegorz Schroeder ◽  
Błażej Gierczyk ◽  
Volodimir Rybachenko
Keyword(s):  
Transfer Reaction ◽  
Acyl Transfer ◽  
Transfer Reactions ◽  
Acetonitrile Solution ◽  
Monovalent Cations ◽  
Sulfur Silicon ◽  
Ionisation Mass Spectrometry ◽  
Acyl Transfer Reaction ◽  
Acyl Transfer Reactions

AbstractTwo bifunctional sulfur-silicon nucleophilic ionophores 3-(trimethoxysilyl)-propanethiol (Nu1) and 3-(tri-2-methoxyethoxysilyl)-propanethiol (Nu2) were used as reagents in the acyl transfer reaction studied by kinetic methods. Nuclear magnetic resonance (NMR) and electro-spray ionisation mass spectrometry (ESI MS) were used for determination of the stoichiometry and stability constants of the complexes made by the podands and lithium or sodium ions in acetonitrile solution.

Correlation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4′-bipyridine cocrystal with their crystal structures

2014 ◽  
Vol 70 (11) ◽  
pp. 1040-1045 ◽  
Author(s):  
Majid I. Tamboli ◽  
Vir Bahadur ◽  
Rajesh G. Gonnade ◽  
Mysore S. Shashidhar
Keyword(s):  
Solid State ◽  
Self Assembly ◽  
Transfer Reaction ◽  
Acyl Transfer ◽  
Transfer Reactions ◽  
Group Transfer ◽  
Hydrogen Bonding Interactions ◽  
Benzoyl Group ◽  
The Stability ◽  
Group Migration

Racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate, C21H18O8,(1), shows a very efficient intermolecular benzoyl-group migration reaction in its crystals. However, the presence of 4,4′-bipyridine molecules in its cocrystal, C21H18O8·C10H8N2,(1)·BP, inhibits the intermolecular benzoyl-group transfer reaction. In(1), molecules are assembled around the crystallographic twofold screw axis (baxis) to form a helical self-assembly through conventional O—H...O hydrogen-bonding interactions. This helical association places the reactive C6-O-benzoyl group (electrophile, El) and the C4-hydroxy group (nucleophile, Nu) in proximity, with a preorganized El...Nu geometry favourable for the acyl transfer reaction. In the cocrystal(1)·BP, the dibenzoate and bipyridine molecules are arranged alternately through O—H...N interactions. The presence of the bipyridine molecules perturbs the regular helical assembly of the dibenzoate molecules and thus restricts the solid-state reactivity. Hence, unlike the parent dibenzoate crystals, the cocrystals do not exhibit benzoyl-transfer reactions. This approach is useful for increasing the stability of small molecules in the crystalline state and could find application in the design of functional solids.

Organocatalytic asymmetric Michael/hemiketalization/acyl transfer reaction of 1,3-propanediones with (E)-2-(2-nitrovinyl)phenols

2019 ◽  
Vol 17 (7) ◽  
pp. 1718-1721 ◽  
Author(s):  
Nimisha Bania ◽  
Subhas Chandra Pan
Keyword(s):  
Transfer Reaction ◽  
Acyl Transfer ◽  
Keto Ester ◽  
Acyl Transfer Reaction

An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between (E)-2-(2-nitrovinyl)phenols and 1,3-propanediones is disclosed to generate products having keto, ester and nitro functionalities.

Bioinspired Synthesis of Chiral 3,4-Dihydropyranones via S-to-O Acyl-Transfer Reactions

2018 ◽  
Vol 20 (6) ◽  
pp. 1584-1588 ◽  
Author(s):  
Hui Jin ◽  
Juyeol Lee ◽  
Hu Shi ◽  
Jin Yong Lee ◽  
Eun Jeong Yoo ◽  
...  
Keyword(s):  
Acyl Transfer ◽  
Transfer Reactions ◽  
Bioinspired Synthesis ◽  
Acyl Transfer Reactions
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