High Quality 1,2,3,4,5-Pentamethylcyclopentadiene In Stock

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High Quality 1,2,3,4,5-Pentamethylcyclopentadiene In Stock

Properties

Description&Application

Mechanism of the Diels-Alder reaction of paramagneticendohedral metallofullerene and 1,2,3,4,5-pentamethylcyclopentadiene has been studied. Three-step large-scale preparation of 1,2,3,4,5-pentamethylcyclopentadiene has been reported. Reaction of 1,2,3,4,5-pentamethylcyclopentadiene (HCp*) with actinide ions in gas phase has been investigated by laser ablation mass spectrometry. It undergoes radical cation catalyzed cycloaddition with electron rich allenes to form Diels-Alder product.

1,2,3,4,5-Pentamethylcyclopentadiene serves as a precursor to the ligand 1,2,3,4,5-pentamethylcyclopentadienyl. It is used as a growth modifier chemical, during metal organic chemical vapor deposition of iron from iron pentacarbonyl. It is used as a ligand in "one-pot" iridium-catalyzed transformation of alcohols to amides. Further, it acts as an electron mediator in the regeneration process of nicotinamide adenine dinucleotide. In addition to this, it undergoes radical cation catalyzed cycloaddition reaction with allenes to get Diels-Alder product.

Preparation Products

Synthesis of cyclopentadienyl-gallium amide compounds Our investigations started by following the reaction of Cp3Ga with an equivalent of ammonia in CDCl3, C6D6 or toluene-d8 by 1 H NMR. Regardless of the solvents used, the elimination of approximately 1.5 equivalents of cyclopentadiene was observed along with the formation of intractable, presumably polymeric materials. Since increasing the steric bulk of the cyclopentadienyl ligands should improve the solubility and prevent oligomerization of the ammonolysis product, gallium substrates with methylsubstituted cyclopentadienyl rings were examined. Reaction of Cp03Ga with NH3 (1:1) in toluene, followed by work up and slow recrystallisation from toluene at  20  C yielded [Cp02Ga(l-NH2)]2 (1) (Eq. (1)). Although the reaction to form compound 1 was reproducible and essentially quantitative whenmonitored in an NMR tube by 1 H NMR spectroscopy, isolation of the compound proved challenging and yields were invariably low. Cp03Ga þ NH3!0:5½Cp02GaNH2 2 ð1Þ þCp0H ð1Þ The use of pentamethylcyclopentadienyl gallium species provides a more reliable route to gallium amide compounds as shown in. Reaction of Cp⁄3Ga with ammonia in toluene afforded [Cp⁄2Ga(l-NH2)]2 (2) in 75% isolated yield. One drawback to this synthetic pathway is the low yields of the Cp⁄3Ga starting material (ca. 40%). [Cp⁄2Ga(l-Cl)]2 presented an appealing alternative since it is prepared in high yield (P70%) and the all of the precious Cp⁄ ligand would be conserved in forming target compound 2. Attempts to prepare compound 2 by reacting [Cp⁄2Ga(l-Cl)]2 with sodium amide in THF or Et2O were unsuccessful, yielding only a complex mixture of products. Instead, [Cp⁄2Ga(l-Cl)]2 was reacted with an equivalent of ammonia to afforded the adduct [Cp⁄2GaCl(NH3)] (3), which was not isolated but was characterized by 1 H NMR spectroscopy (d 1.76 (s, 30H, C5Me5), 1.08 (bs, 2.8H, NH3) ppm). An in situ dehydrohalogenation reaction of 3 with t-butyllithium afforded compound 2 with an isolated yield of 47%. In the absence of t-butyllithium, compound 3 eliminated Cp⁄ H slowly (days) at room temperature or in a few hours at 80  C to form [Cp⁄ (Cl)Ga(l-NH2)]3 (4). If not isolated, compound 4 formed an unidentifified precipitate, possibly a higher aggregate species, over time.

Company Information

Mascot I.E.Co.,Ltd. is founded in 2006, with registered capital at 10million RMB. It is an export-oriented enterprise, We have been dedicated to providing stable-quality Fine chemicals and high-efficient professional exporting service.

Mascot has an excellent R & D team with experience over 293 years as well as well-equipped R & D laboratory and cooperated OEM plants in Jiangsu、 Jiangxi、Shandong province etc. We are committed to stable- supplying & development Fine chemicals, which are widely applied in Pharmaceutical industry/Electronic Chemical/ Polyimide monomer etc.

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