57517-81-4Relevant academic research and scientific papers
Stereochemical analysis of β-keto sulfoxides by circular dichroism
Górecki, Marcin,Capozzi, Maria Annunziata M.,Albano, Gianluigi,Cardellicchio, Cosimo,Di Bari, Lorenzo,Pescitelli, Gennaro
, p. 29 - 42 (2018)
Three β-keto sulfoxides (1–3) were synthesized in enantiopure form and investigated by means of circular dichroism (CD) spectroscopy, both in electronic and vibrational range (ECD, VCD), in combination with quantum chemical calculations. For compound 2, t
New insights into the titanium-mediated enantioselective oxidation of fluorinated aryl benzyl sulfides and aryl phenacyl sulfides
Capozzi, Maria Annunziata M.,Frascaro, Vanni,Pescitelli, Gennaro,Cardellicchio, Cosimo
, p. 2406 - 2412 (2019/03/21)
A fruitful switch from tert-butyl to cumene hydroperoxide was able to overcome a difficulty arose in the enantioselective oxidation of fluorinated aryl benzyl sulfide with hydroperoxides in the presence of a titanium/(S, S)-hydrobenzoin catalyst. New expe
Photochemical Induced Cyclisation of β-Keto Sulfides to Cycloalkanones
Bahari, Kamarudin B.,Deodhar, Dinker J.,Hesabi, Masoud-M.,Hill, John,Kosmirak, Mario,et al.
, p. 2393 - 2398 (2007/10/02)
On UV irradiation, β-keto sulfides ArSCH2COPh (Ar = C6F5, C6CL5) cleaved to radicals ArS* and PhCOCH2* which, in one case (Ar = C6F5), were trapped by 1,1-diphenylethylene as the adduct PhCOCH2CH2C(Ph)2SC6F5.With diethyl ether as the solvent the major product was the monothioacetal ArSCH(Me)OEt.The keto sulfide 4-MeSO2C6H4SCH2COPh behaved similarly on irradiation in tetrahydrofuran.Irradiation of the unsaturated β-keto sulfides CH2=CH2COCH2SAr resulted in homolysis of the CH2-S bond to give a 2-oxohex-5-enyl radical, which subsequently cyclised; 4-(pentafluorophenylsulfanyl)cyclohexanone (when Ar = C6F5) and cyclohexanone (when Ar = p-tolyl) were the major products.With β-keto sulfides containing an aryl substituent, ethyl 2-benzyl-2-methyl-3-oxo-4-(pentafluorophenylsulfanyl)butanoate and 1,3-bis(p-tolylsulfanyl)propanone, irradiation resulted in cyclisation with loss of the sulfanyl substituent (probably involving electron transfer) to give 3-ethoxycarbonyl-3-methyl-1,2,3,4-tetrahydronaphthalen-2-one and 6-methylthiochroman-3-one, respectively, in high yield.
