78725-90-3Relevant academic research and scientific papers
Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides
Xie, Shimin,Su, Lebin,Mo, Min,Zhou, Wang,Zhou, Yongbo,Dong, Jianyu
, p. 739 - 749 (2021/01/09)
An alternative thioesterification reaction via copper-catalyzed oxidative coupling of readily available aroylhydrazides with disulfides is developed, in which oxidative expulsion of N2 overcomes the activation barrier between the carboxylic acid derivativ
Convenient route to thiocarbonates from alcohols, thiols, and triphosgene
Movassagh, Barahman,Soleiman-Beigi, Mohammad
experimental part, p. 3467 - 3471 (2011/02/22)
An efficient and simple one-pot, three-component procedure has been introduced for the preparation of various thiocarbonates from thiols, alcohols, and triphosgene in dichloromethane. Copyright Taylor & Francis Group, LLC.
A new method for synthesis of S-aryl-O-alkyl thiolcarbonates: Selenium-catalyzed reaction of alcohols with carbon monoxide and diaryl disulfides
Nishiyama, Yutaka,Maehira, Ken,Nakase, Junko,Sonoda, Noboru
, p. 7415 - 7417 (2007/10/03)
A unique catalytic ability of selenium has been developed. When alcohols were allowed to react with diaryl disulfides in the presence of a catalytic amount of selenium under a pressurized carbon monoxide, S-aryl-O-alkyl thiolcarbonates were obtained in moderate to good yields.
Chemistry of trichlorofluromethane: Synthesis of chlorofluromethyl phenyl sulfone and fluoromethyl phenyl sulfone and some of their reactions
Saikia,Tsuboi
, p. 643 - 647 (2007/10/03)
It was observed that the reaction of CFCl3 with thiophenoxide gave only 10% of the corresponding thioether. On the other hand, these thioethers could be prepared in excellent yield from diaryl disulfides and CFCl3 in the presence of sodium hydroxymethanesulfinate in aqueous DMF at 4 atm pressure of nitrogen. Dechlorination of the thioether (PhSCFCl2) with different reducing agents were studied. Most of the reducing agents eliminated both fluorine and chlorine functionalities or gave the hydrolyzed products. But its sulfone on treatment with Zinc in methanol gave monochlorofluoromethyl and fluoromethyl phenyl sulfone in good yields. Darzens reaction of these compounds was also studied.
Kinetics and mechanism of the aminolysis of O-ethyl S-aryl thiocarbonates in acetonitrile
Oh, Hyuk Keun,Lee, Yun Ho,Lee, Ikchoon
, p. 131 - 135 (2007/10/03)
The Kinetics and mechanism of the reactions of O-ethyl S-(Z)aryl thiocarbonates with (X)benzylamines in acetonitrile at 45.0 °C are studied. Relatively small values of βx (βnuc) = 0.6 to approximately 0.8 and βz (βlg) = -0.5 to approximately -0.7 together with a negative cross-interaction constant ρxz (= -0.47) and failure of the reactivity-selectivity principle (RSP) are interpreted to indicate a concerted mechanism. The normal kinetic isotope effects (kH/kD = 1.3 to approximately 1.8) involving deuterated benzylamine nucleophiles suggest a hydrogen-bonded, four-center-type transition state.
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.
Cleavage of carbon-sulfur bonds in the synthesis of α-haloalkyl carbonates
Hatlelid, Jostein,Benneche, Tore,Undheim, Kjell
, p. 1041 - 1044 (2007/10/03)
α-Chloroalkyl and α-bromoalkyl carbonates have been prepared by cleavage of α-arylthioalkyl carbonates with sulfuryl chloride or bromine, respectively. The α-arylthioalkyl carbonates are prepared by reaction of the hemithioacetal 1 with chloroformates or by a destannylative tin-Pummerer rearrangement of α-stannyl sulfoxides. Acta Chemica Scandinavica 1996.
The Mechanism of Thermal Eliminations. Part 19. Rate Data for Pyrolysis of S-Aryl O-Ethyl Thiocarbonates: the Relative Abilities of Oxygen and Sulphur to Transmit Electronic Effects
Al-Awadi, Nouria,Taylor, Roger
, p. 1581 - 1584 (2007/10/02)
Rates of thermal decomposition of a range of S-aryl O-ethyl thiocarbonates have been measured over a 50 degree C range for each compound, between 722.6 and 671.4 K.The compounds are less reactive than the corresponding aryl ethyl carbonates by a factor of ca. 2.0 at 679 K, owing to the smaller -I effect of SAr relative to OAr.This provides further conformation that the reactivity of esters towards thermal elimination parallels the extent of electron withdrawal by the group attached to the acyl carbon atom.The reaction gives a good Hammet correlation with ?0 values, and ρ is 0.26 at 700 K, significantly greater than the value for the corresponding aryl ethyl carbonates.Thus sulphur is a better transmitter of electronic effects than is oxygen, and this transmission order, previously observed in studies in solution, is not a result of solvation phenomena.The ortho-methoxy substituent deactivates in thiocarbonate pyrolysis in contrast to its activation in carbonates.This probably arises from through-space p? --> d? bonding in the former compounds.An improved gold-plated stainless steel pyrolytic reactor is described.
