28145-62-2Relevant academic research and scientific papers
From carboxylic acids to the trifluoromethyl group using BrF3
Cohen, Or,Mishani, Eyal,Rozen, Shlomo
experimental part, p. 3579 - 3582 (2010/07/04)
Organic trifluoromethyl derivatives were made from aromatic and aliphatic carboxylic acids by transforming them first into the corresponding dithioesters followed by reaction with bromine trifluoride under mild conditions (0 °C, 2 min).
Convenient and efficient synthesis of thiol esters using zinc oxide as a heterogeneous and eco-friendly catalyst
Bandgar, Babasaheb Pandurang,More, Parmeshwar Eknath,Kamble, Vinod Tribhuvannathji,Sawant, Sanjay Suresh
experimental part, p. 1006 - 1010 (2009/04/05)
A catalytic method was developed to synthesize thiol esters from the reaction of acyl chlorides and thiols using zinc oxide as a catalyst under solvent-free conditions at room temperature. Mild reaction conditions, short reaction time, excellent yields of products and recyclability of the catalyst are noteworthy features of this methodology. CSIRO 2008.
Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides
Aitken, R. Alan,Armstrong, Jill M.,Drysdale, Martin J.,Ross, Fiona C.,Ryan, Bruce M.
, p. 593 - 604 (2007/10/03)
A range of 18 alkoxycarbonyl sulfinyl phosphorus ylides 9 have been prepared and their behaviour upon flash vacuum pyrolysis (FVP) at 600 deg C examined. For R1 = H, Me and Et they lose Ph3PO and in some cases Ph3P to give mixtures of products including the alkenyl sulfides 10, the sulfides 11, the disulfides 12 and the thioesters 14. The alkenyl sulfides 10 most likely arise from intramolecular insertion of the alkoxycarbonyl sulfenyl carbenes resulting from loss off Ph3PO to produce β-lactones which then lose CO2 and this is supported by the results from 13C labelled ylides. Possible mechanisms for the formation of 11 and 14 are also presented and the feasibility of various steps has been examined by preparation and pyrolysis of the proposed intermediates. In contrast, pyrolysis of the ylides 9 where R1 = Ph and the tert-butoxycarbonyl ylides 30 leads mainly to complete fragmentation with loss of Ph3PO and benzyl alcohol or 2-methylpropan-2-ol and does not give any useful sulfur-containing products. Four alkoxy-carbonyl sulfonyl diazo compounds 33 have been prepared and in three cases they give the alkenyl sulfones 34 upon FVP at 400 deg C, probably by an intramolecular insertion and decarboxylation process analogous to the formation of 10 from 9. On the other hand the alkoxycarbonyl carbenes produced by FVP of the amino acid-derived diazo compounds 35 undergo alternative proocesses with no sign of β-lactone formation. Fully assigned 13C NMR data are presented for 13 of the ylides.
Zinc promoted convenient and general synthesis of thiol esters
Meshram,Reddy, Gondi Sudershan,Bindu, K. Hima,Yadav
, p. 877 - 878 (2007/10/03)
Synthesis of thiol esters from acyl chlorides and thiols in the presence of activated zinc is described. The recovery of zinc and its reuse makes the procedure more economic.
A Novel Method for Converting Aromatic Acids into Trifluoromethyl Derivatives using BrF3
Rozen, Shlomo,Mishani, Eyal
, p. 2081 - 2082 (2007/10/02)
Aryltrifluoromethyl derivatives are obtained in good yields from the corresponding aryl carboxylic acids by reacting their dithionic esters with BrF3 under very mild conditions.
