56772-75-9Relevant academic research and scientific papers
Straightforward chemoselective access to unsymmetrical dithioacetals through a thiosulfonate homologation-nucleophilic substitution sequence
Ielo, Laura,Pillari, Veronica,Gajic, Natalie,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 12395 - 12398 (2020/10/30)
A sequential C1-homologation-nucleophilic substitution tactic is presented for the preparation of rare unsymmetrical dithioacetals. The judicious selection of thiosulfonates as convenient sulfur electrophilic sources - upon the homologation event conducted on an intermediate a-halothioether - guarantees the release of the non-reactive sulfonate group, thus enabling the subsequent nucleophilic displacement with an external added thiol [(hetero)- aromatic and/or aliphatic]. Uniform high yields and excellent chemocontrol were deduced during the extensive scope study, thus documenting the versatility of the direct technique for the preparation of these unique and manipulable materials.
Synthesis of dithioacetals and oxathioacetals with chiral auxiliaries
Zaidi, Javid H.,Naeem, Fazal,Khan, Khalid M.,Iqbal, Rasfaid,Zia-Ullah
, p. 2641 - 2653 (2007/10/03)
One-pot synthesis of dithioacetals as well as an efficient method for oxathioacetal is reported. Additionally, some chiral auxiliaries were used to synthesize enantiomerically pure dithioacetals and oxathioacetals.
Synthesis and novel reactivity of halomethyldimethylsulfonium salts
Xu, Yuelian,Fletcher, Michelle,Dolbier Jr., William R.
, p. 3460 - 3465 (2007/10/03)
Iodomethyl-, chloromethyl-, and fluoromethyldimethylsulfonium salts, 4b-d, have been synthesized and are observed to be highly reactive molecules that exhibit extraordinary diversity with respect to the nature of their reactivity, undergoing facile direct substitution (SN2) reactions, but also being highly susceptible to electron-transfer reactions. Cyclic voltametry experiments indicated that the iodomethyldimethylsulfonium compound, 4b, is a potent electron acceptor, even surpassing the reactivity of perfluoro-n-alkyl iodides in that capacity. The iodo- and chloromethyldimethylsulfonium salts, 4b,c, as well as the analogous iodomethyltrimethylammonium salt, 3a, are shown to be reactive SET acceptors.
An efficient synthesis of unsymmetrical dithioacetals from sulfoxides and thiols by the magnesium amide-induced pummerer-type reaction
Kobayashi, Kazuhiro,Kawakita, Masataka,Akamatsu, Hideki,Morikawa, Osamu,Konishi, Hisatoshi
, p. 2645 - 2647 (2007/10/03)
It has been found that the reactions of sulfoxides bearing hydrogen(s) at the α-position (R 1 SOCHR 2R 3: R 1 = alkyl or Ph; R 2 = H, alkyl, or Ph; R 3 = H or Me) with thiols (R 4SH: R 4 = alkyl or aryl) in the presence of the (diisopropylamino)magnesium
Reactions of Sulfoxides with Magnesium Amides. Transformations of Sulfoxides into Sulfides, Dithioacetals and Vinyl Sulfides
Kobayashi, Kazuhiro,Kawakita, Masataka,Yokota, Kouichi,Mannami, Tohru,Yamamoto, Koji,et al.
, p. 1401 - 1408 (2007/10/02)
The reactions of sulfoxides with magnesium amides generated in situ from the reaction of ethylmagnesium bromide and seconday amines, such as diisopropylamine (DIPA) or 2,2,6,6-tetramethylpiperidine (TMP) in diethyl ether, were examined.Diaryl sulfoxides were heated with the diisopropylaminomagnesium reagent in diethyl ether to give the corresponding diaryl sulfides in 42-52percent yields.Sulfoxides bearing hydrogens at the α-position only(RSOCH2R1) reacted with the tetramethylpiperidinomagnesium reagent at room temperature to produce the corresponding dithioacetals (RSCHR1SR) in 47-86percent yields.The treatment of sulfoxides bearing hydrogens both at the α-and β-positions (RSOCHR1CHR2R3) with the magnesium amides at room temperature afforded the corresponding vinyl sulfides (RSCR1=CR2R3) in 52-72percent yields accompanying 2.3-27percent yields of the corresponding dithioacetals.The pathways leading to the products involving the formation of the sulfur-stabilized carbonium ion intermediates are discussed.
SPONTANEOUS -SIGMATROPIC REARRANGEMENT OF S-ARYLTHIOSULFONIUM YLIDS FORMED IN THE REACTION OF ARYLSULFENYL CHLORIDES WITH METHYLTHIOMETHYLTRIMETHYLSILANE
Gassman, Paul G.,Miura, Takashi
, p. 4787 - 4790 (2007/10/02)
A new -sigmatropic rearrangement of thiosulfonium ylids yields ortho-methylthiomethylthiophenols.The ylids were generated through the cleavage of a C-Si bond with chloride anion.
Reaction of Pummerer Rearrangement Intermediates with Sulfides and Thiols. Synthesis of Sulfonium Salts and Dithioacetals
Tanikaga, Rikuhei,Hiraki, Yuji,Ono, Noboru,Kaji, Aritsune
, p. 41 - 42 (2007/10/02)
Sulfides (5) and thiols (6) react instantly with the Pummerer rearrangement intermediates (3) at 0 deg C to give sulfonium salts (7) and dithioacetals (8), respectively.
REACTIONS OF TETRAPHENYLANTIMONY MERCAPTIDES
Wardell, James L.,Grant, Douglas W.
, p. 121 - 130 (2007/10/02)
Reactions of tetraphenylantimony mercaptides, Ph4SbSC6H4Y, with electrophilic species in chlorocarbon solutions are reported.With chloromethyl methyl sulphide, allyl halides, sulphenyl halide, acyl halides, halogens, and triphenyltin chloride, ready and complete halide-mercaptide exchanges occur.No allylic rearrangement is found in the reaction with trans-PhCH=CHCH2Br.In a competition reaction for ClCH2SMe, Ph4SbSC6H5 was shown to be only slightly (ca. 1.2 times) more reactive than Ph4SbSC6H4OMe-p.The initial sulphur-containing product of reaction with p-toluenesulphonyl chloride, namely the thiosulphonate, p-MeC6H4SO2SC6H4Y, reacts further with Ph4SbSC6H4Y to produce the disulphide, (YC6H4S)2.Benzoyl peroxide and Ph4SbSC6H4 provide PhSbOCOPh and disulphide.
Prostaglandin analogues
-
, (2008/06/13)
Prostaglandins of the formula: STR1 wherein A represents a grouping of the formula: STR2 X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R represents a hydrogen atom or a straight- or branched-chain alkyl group containing f
