120553-08-4Relevant articles and documents
Phase-vanishing method applied to condensation reactions using TiCl4
Adachi, Yusuke,Kuniyoshi, Kenji,Matsubara, Hiroshi
, p. 100 - 105 (2017/04/10)
The phase-vanishing (PV) method using perfluorohexanes as the phase screen was applied to the aldol condensation using TiCl4 as the Lewis acid. A special test tube was used, in which an interface between the fluorous and organic layers was stirred, and cyclohexanone was treated with two equivalents of benzaldehyde derivatives under PV conditions to afford corresponding 2,6-dibenzylidencyclohexanone in good yields. The formyl-methylenation of ketones with triethylamine using TiCl4 was also demonstrated by the PV method.
A Weinreb Amide Based Building Block for Convenient Access to β,β-Diarylacroleins: Synthesis of 3-Arylindanones
Tiwari, Praveen Kumar,Aidhen, Indrapal Singh
, p. 2637 - 2646 (2016/06/08)
Towards the synthesis of symmetrical and unsymmetrical β,β-diarylacroleins for assembling diarylmethine fragments present in biologically important molecules, we have developed a new Weinreb amide (WA) based building block, derived from propiolic acid. The WA functionality present in this compound allowed the sequential addition of various arylmagnesium bromide reagents in a controlled manner. The developed methodology for the access to β,β-diarylacroleins has been utilised for the synthesis of biologically important 3-arylindanone molecules. Synthesis of both symmetrical and unsymmetrical β,β-diarylacrolein and diarylmethine fragments, have been achieved via easily accessible and hitherto unknown Weinreb Amide (WA) based building block 11. The WA functionality allowed the sequential addition of nucleophiles such as arylmagnesium bromide in a controlled manner, which has enabled the synthesis of an important 3-arylindanone molecule.
New Ag(I)-iminophosphorane coordination polymers as efficient catalysts precursors for the MW-assisted meyer-schuster rearrangement of propargylic alcohols in water
Garcia-Alvarez, Joaquin,Diez, Josefina,Vidal, Cristian,Vicent, Cristian
, p. 6533 - 6542 (2013/07/19)
Treatment of the N-thiophosphorylated iminophosphorane ligands (PTA)=NP(=S)(OR)2 [PTA = 1,3,5-triaza-7-phosphaadamantane, 3a and 3b] and (DAPTA)=NP(=S)(OR)2 [DAPTA = 3,7-diacetyl-1,3,7-triaza-5- bicyclo[3.3.1]nonane, 4a and 4b] with an equimolecular amount of AgSbF 6 leads to high-yield formation of the new one-dimensional coordination polymers [Ag{μ2-N,S-(PTA)=NP(=S)(OR) 2}]x[SbF6]x (5a and 5b) and [Ag{μ2-O,S-(DAPTA)=NP(=S)(OR)2}]x[SbF 6]x (6a and 6b), respectively. These new (iminophosphorane)silver(I) coordination polymers are efficient catalyst precursors for the Meyer-Schuster isomerization of both terminal and internal alkynols. Reactions proceeded in water, under aerobic conditions and using microwave irradiation as heating source, to afford the corresponding α,β-unsaturated carbonyl compounds in excellent yields, without the addition of any cocatalyst. Remarkably, it should be noted that this catalytic system can be recycled up to 10 consecutive runs (1st cycle 45 min, 99%; 10th cycle 6 h, 97%). ESI-MS analysis of 5a in water has been carried out providing valuable insight into the monomeric active species responsible for catalytic activity in water.
