4102-50-5Relevant academic research and scientific papers
Phenyl piperazidine thioether and preparation method thereof
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Paragraph 0027; 0032, (2017/07/20)
The invention relates to a phenyl piperazidine thioether and a preparation method thereof. The compound is 4,6-dimethyl-1,3-bis-2,2'-phenyl piperazidine thioether and is synthesized by taking 1,3-dimethyl benzene used as an initial raw material through a
Desulfonyloxyiodination of arenesulfonic acids with mCPBA and molecular iodine
Suzuki, Yuhsuke,Ishiwata, Yoshihide,Moriyama, Katsuhiko,Togo, Hideo
experimental part, p. 5950 - 5953 (2010/11/21)
Treatment of p-alkylbenzenesulfonic acids with mCPBA and molecular iodine gave p-alkyliodobenzenes in good to moderate yields via electrophilic ipso-substitution by the iodonium species (I+) formed. This desulfonyloxyiodination was promoted by the addition of a catalytic amount of iodoarenes, such as o-iodobenzoic acid. The same treatment of dimethylbenzenesulfonic acids and trimethylbenzenesulfonic acids with mCPBA and molecular iodine proceeded smoothly both in the absence and in the presence of o-iodobenzoic acid to provide the corresponding monoiodo-dimethylbenzene and diiodo-dimethylbenzene, and diiodo-trimethylbenzene and triiodo- trimethylbenzene, in good to moderate yields, respectively. On the other hand, the same desulfonyloxyiodination of benzenesulfonic acid and p-chlorobenzenesulfonic acid with mCPBA and molecular iodine proceeded only in the presence of o-iodobenzoic acid to generate iodobenzene and p-chloroiodobenzene, respectively, in moderate yields.
2,4,6,8-tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione as a mild and convenient reagent for iodination of aromatic compounds
Chaikovski,Filimonov,Yagovkin,Ogorodnikov
, p. 2411 - 2415 (2007/10/03)
2,4,6,8-Tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (tetraiodoglycoluril) is a convenient reagent for preparative iodination of benzene, alkylbenzenes, polycyclic hydrocarbons, aromatic amines, and phenol ethers in organic solvents under mild conditions.
Reactivity and synthetic utility of 1-(arenesulfonyloxy) benziodoxolones
Muraki, Takahito,Togo, Hideo,Yokoyama, Masataka
, p. 2883 - 2889 (2007/10/03)
The reactivity and synthetic use of 1-(arenesulfonyloxy)benziodoxolones were studied. In the presence of iodine, 1-(arenesulfonyloxy)benziodoxolones iodinated various aromatics to give iodoarenes in moderate to good yields. In particular, 1-(p-chlorobenzenesulfonyloxy)benziodoxolone showed the best reactivity. Using a halide salt such as lithium bromide or lithium chloride instead of iodine, the corresponding aryl bromides and chlorides were also obtained in good yields. In the absence of aromatics, 1- (arenesulfonyloxy)benziodoxolones gave rise to desulfonyloxyiodination reactions to give the corresponding aryl iodides via electrophilic ipso substitution on the aromatic rings. Furthermore, the l-(p- toluenesulfonyloxy)benziodoxolone/iodine system iodotosyloxylated alkynes in good yields. These reactions proceeded via the formation of arenesulfonyl hypoiodites.
Improved, Acid-catalyzed Iodinating Procedures for Activated Aromatics with (Diacetoxyiodo)benzene as the Oxidant
Kryska, Anna,Skulski, Lech
, p. 2501 - 2517 (2007/10/03)
Improved procedures for the oxidative, acid-catalyzed iodination of benzene, iodobenzene and several activated aromatics are presented to give mono-, di-, or triiodinated products in 40-82 percent yields. The reactions proceeded at room temperature in the anhydrous systems: arene or hetarene/diiodine/(diacetoxyiodo)benzene (2)/glacial acetic acid/acetic anhydride, acidified with catalytic amounts of concd. (98 percent) H2SO4. Within at most 15 minutes the iodine coloration faded; the following workups are explained. A similar treatment with dibromine gave tribromomesitylene (65 percent), dibromodurene (62 percent), and 2,7-dibromofluoren-9-one (73 percent). A review on the aromatic halogenation reactions with organic trivalent iodine reagents as the oxidants is presented below.
The direct iodination of arenes with chromium(VI) oxide as the oxidant
Lulinski, Piotr,Skulski, Lech
, p. 1665 - 1669 (2007/10/03)
An easy and cheap laboratory method is presented for the direct mono- and diiodination of a number of activated and deactivated arenes. The main iodination reactions occurred at the temperatures not exceeding 65°C for 0.5-12 h in the anhydrous, strongly acidic liquid system, I2/AcOH/Ac2O/H2SO4, in the presence of prior dissolved CrO3 used as the oxidant. The yields of the pure iodinated products varied from 31% (for 3,5- diiodobenzoic acid) up to 90% (for 4-iodoanisole). So far, benzonitrile and some oxidizable aromatics, e.g. naphthalene, fluorene, xanthene, and thiophene, have been found to be unsuitable for the effective iodination. Nevertheless, this novel, simple method of direct iodination is worthy to be extended to other appropriate aromatics.
Halogenation Using Quaternary Ammonium Polyhalides. XIV. Aromatic Bromination and Iodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Tanaka, Toshio,Fujisaki, Shizuo,Okamoto, Tsuyoshi
, p. 439 - 443 (2007/10/02)
The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave brome- or iodo-substituted arenes in good yield, respectively.
A SIMPLE METHOD FOR THE IODINATION OF AROMATIC COMPOUNDS
Merkushev, E. B.,Yudina, N. D.
, p. 2320 - 2322 (2007/10/02)
The iodine - (trifluoroacetoxyiodo)benzene system is effective for the iodination of aromatic compounds, alkylbenzenes, various polynuclear aromatic hydrocarbons, halogenobenzenes, and some heterocyclic compounds.Trifluoroacetyl hypoiodite, which is a source of electrophilic iodine, is probably formed initially.Trifluoroacetyl hypoiodite can be generated in situ from (diacetoxyiodo)benzene and trifluoroacetic acid.
