625-60-5Relevant articles and documents
Acyl iodides in organic synthesis. Reaction of acetyl iodide with Dialkyl sulfides and disulfides
Vlasova,Grigor'Eva,Voronkov
, p. 46 - 48 (2013/03/28)
Reactions of acetyl iodide with dialkyl and dialkenyl sulfides RSR (R = Et, Bu, CH2=CH, CH2=CHCH2) and with disulfides RSSR (R = Pr, C6H13, PhCH2) were studied. Dialkyl sulfides reacted with MeCOI to give the corresponding alkyl ethanethioates and alkyl iodides as a result of cleavage of the S-C bond. The reactions of acetyl iodide with divinyl and diallyl sulfides involved addition across the double bond and subsequent polymerization of 1-alkenylsulfanyl-2(3)- iodoalkyl methyl ketones. Dialkyl disulfides RSSR (R = Pr, C6H 13) and dibenzyl disulfide reacted with acetyl iodide via cleavage of the S-S bond to produce the corresponding ethanethioates and organylsulfenyl iodides. The latter underwent disproportionation to form the initial disulfide and molecular iodine.
Silver triflate catalyzed acetylation of alcohols, thiols, phenols, and amines
Das, Rima,Chakraborty, Debashis
experimental part, p. 1621 - 1625 (2011/06/25)
A variety of alcohols, thiols, phenols, and amines were subjected to acetylation reaction using acetic anhydride in the presence of catalytic quantity of silver triflate. The method described has a wide range of applications, proceeds under mild conditions, does not involve cumbersome workup, and the resulting products are obtained in high yields within a reasonable time. Georg Thieme Verlag Stuttgart · New York.
Facile catalyzed acylation of alcohols, phenols, amines and thiols based on ZrOCl2·8H2O and acetyl chloride in solution and in solvent-free conditions
Ghosh, Rina,Maiti, Swarupananda,Chakraborty, Arijit
, p. 147 - 151 (2007/10/03)
Acylation of heteroatoms (O, N and S) with acetyl chloride based on the use of a catalytic amount of the moisture stable, inexpensive ZrOCl 2?8H2O, proceeds efficiently producing the corresponding acylated products in excellent yields.
Facile catalyzed acylation of heteroatoms using BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride
Ghosh, Rina,Maiti, Swarupananda,Chakraborty, Arijit
, p. 6775 - 6778 (2007/10/03)
Acylation of a variety of alcohols, phenols, aliphatic and aromatic amines, a thiol and a thiophenol proceeds efficiently using BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride in a solvent or under solventless conditions, furnishing the corresponding acylated derivatives in very good to excellent yields.
Transacylation of α-Aryl-β-keto Esters
Nishiwaki, Nagatoshi,Nishida, Daisei,Ohnishi, Tetsuya,Hidaka, Fumie,Shimizu, Satoru,Tamura, Mina,Hori, Kazushige,Tohda, Yasuo,Ariga, Masahiro
, p. 8650 - 8656 (2007/10/03)
The acyl group of an α-aryl-β-keto ester was readily transferred to N-, O-, and S-nucleophiles. The transacylation from arylated diethyl 3-oxoglutarate to amines led to unsymmetrical malonic acid amide esters in high yields. The present reaction proceeded under mild conditions without formation of detectable byproducts. Only simple experimental manipulations were required. This reaction was also found to be sensitive to steric factors, which enabled the chemoselective monoacylation of diamines and amino alcohols without any modifications such as protection.
Mutation of cysteine-295 to alanine in secondary alcohol dehydrogenase from thermoanaerobacter ethanolicus affects the enantioselectivity and substrate specificity of ketone reductions
Heiss, Christian,Laivenieks, Maris,Zeikus,Phillips, Robert S.
, p. 1659 - 1666 (2007/10/03)
The mutation of Cys-295 to alanine in Thermoanaerobacter ethanolicus secondary alcohol dehycrogenase (SADH) was performed to give C295A SADH, on the basis of molecular modeling studies utilizing the X-ray crystal structure coordinates of the highly homologous T. brockii secondary alcohol dehydrogenase (YKF.PDB). This mutant SADH has activity for 2-propanol comparable to wild-type SADH. However, the C295A mutation was found to cause a significant shift of enantioselectivity toward the (S)-configuration in the reduction of some ethynylketones to the corresponding chiral propargyl alcohols. This result confirms our prediction that Cys-295 is part of a small alkyl group binding pocket whose size determines the binding orientation of ketone substrates, and, hence, the stereochemical configuration of the product alcohol. Furthermore, C295A SADH has much higher actifity towards t-butyl and some α-branched ketones than does wild-type SADH. The C295A mutation does not affect the thioester reductase activity of SADH. The broader substrate specificity and altered stereoselectivity for C295A SADH make it a potentially useful tool for asymmetric reductions. Copyright
Electrochemical carbon dioxide fixation to thioesters catalyzed by [Mo2Fe6S8(SEt)9]3-
Komeda, Nobutoshi,Nagao, Hirotaka,Matsui, Tatsuji,Adachi, Gin-Ya,Tanaka, Koji
, p. 3625 - 3630 (2007/10/02)
A controlled potential electrolysis at -1.55 V versus SCE of CO2-saturated CH3CN containing (Et4N)3[Mo2Fe6S 8(SEt)9], CH3C(O)SEt, Bu4NBF4, and Molecular Sieve 3A as a desiccant produced CH3C(O)COO- with a current efficiency of 27%. Similar electrolysis using C2H5C(O)SEt and C6H5C(O)SEt also catalytically afforded C2H5C(O)COO- and C6H5C(O)COO- with current efficiencies of 49 and 13%, respectively. These reactions are strongly inhibited by the presence of not only H2O but also excess EtS-. Strong acylating agents such as acetyl chloride, acetic anhydride, acetyl sulfide, and acetylimidazole in place of CH3C(O)SEt caused decomposition of [Mo2Fe6S8(SEt)9]3-, and no CH3C(O)COO- was formed under the same electrolysis conditions.
A Formylcarbonium Ion Synthon. Synthesis of 3-Thio-Substituted 2-Amino Acids and Thio-Substituted Enamines from 2-Acyloxyacrylonitriles
Oku, Akira,Hori-ie, Naofumi,Harada, Toshiro
, p. 609 - 612 (2007/10/02)
The utilization of 2-acyloxy-3-phenylthiopropionitriles (2) which were prepared by the Michael addition of thiophenol to 2-acyloxyacrylonitriles (CH2=C(CN)OCOR), as a formylcarbonium ion synthon, was demonstrated by the transformation of 2 into S-phenylcysteine and 2-phenylthio enamines.
HOMOLYTIC TRANSFORMATIONS OF 1,3-OXATHIOLANES AT HIGH PRESSURE
Trifonova, V. N.,Zorin, V. V.,Batyrbaev, N. A.,Makarova, Z. G.,Zlotskii, S. S.,et al.
, p. 1386 - 1389 (2007/10/02)
The effect of high pressure was studied on the rate and direction of the homolytic transformations of 1,3-oxathiolanes.Pressure reduces the rate of the transformation of 2-methyl- and 2-isopropyl-1,3-oxathiolanes to ethyl and 2-chloroethyl thoiacylates in the presence of CCl4 to a greater extent than the initiation rate in the system.The selectivity of the formation of the reaction product which is formed more rapidly at normal pressure is increased in the competing homolytic transformations of 2-methyl- and 2-isopropyl-1,3-oxathiolanes to the corresponding ethyl thioacylates with increasing pressure.The yield of the cyclic adduct, 2-methyl-2-hexyl-1,3-oxathiolane, relative to that of linear octyl thioacetate is increased in the homolytic addition of 2-methyl-1,3-oxathiolane to 1-hexane with increasing pressure.
