1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene

Base Information

• Chemical Name: 1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene
• CAS No.: 51533-82-5
• Molecular Formula: C₁₃H₁₈Ge
• Molecular Weight: 246.876
• Mol file: 51533-82-5.mol

Synonyms:1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene

Chemical Property of 1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene

There total 6 articles about 1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

methylmagnesium bromide (75-16-1) + phenylmagnesium bromide (100-58-3) + 1,1-dichloro-3,4-dimethyl-1-germacyclopent-3-ene (5764-64-7) → 1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene (51533-82-5)

Guidance literature:

In diethyl ether; under N2 atm. to soln. 1,1-dichloro-3,4-dimethyl-1-germacyclopent-3-ene in Et2O at 0°C PhMgBr in Et2O was added over 1 h, stirred at roomtemp. for 20 h, MeMgBr in Et2O was added over 1 h and stirred under ref lux for 3 h; react. mixt. was cooled and hydrolized with aq. NH4Cl, org. layer was washed with water and aq. sodium bicarbonate and dried over MgSO4, solventwas removed in vacuo, residue was distilled in vacuo (103-105°C at 0.3 mm Hg);

DOI:10.1139/V06-107

Reference yield: 60.0%

methyl(phenyl)bis(trimethylsilyl)germane (134847-65-7) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → 1,1,1,2,2,2-hexamethyldisilane (1450-14-2) + 1,3,4-trimethyl-1-(trimethylsilyl)-1-germacyclopent-3-ene (134847-66-8) + (2,3-dimethyl-3-butenyl)methyl(trimethylsilyl){o-(trimethylsilyl)phenyl}germane (134847-67-9) + trimethylphenylsilane (768-32-1) + 1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene (51533-82-5)

Guidance literature:

In pentane; Irradiation (UV/VIS); (N2), 1.5 h irradiated; column chromatography; elem. anal., NMR, mass. spectra;

DOI:10.1021/om00054a046

Reference yield: 2.0%

methylphenylchlorogermane (58276-72-5) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → 1,3,4-trimethyl-1-phenyl-1-germacyclopent-3-ene (51533-82-5)

Guidance literature:

With triethylamine; In benzene; byproducts: (C2H5)3NHCl; Et3N adding in excess to germane soln. in benzene, stirring at ambient temp., Et3NHCl filtering off, ligand adding, heating for 6 h at 130°C;

DOI:10.1016/S0022-328X(00)87639-1

upstream raw materials:

1,2-dimethyl-1,1,2,2-tetraphenylgermane

2,3-dimethyl-buta-1,3-diene

methylphenylchlorogermane

methylmagnesium bromide

Downstream raw materials:

acetoxymethylphenylgermane

Ge(CH₃)(C₆H₅)C₂H₃C(CH₃)CH₂

Ge(CH₃)(C₆H₅)C₂HC(CH₃)3

Ge(CH₃)(C₆H₅)N(C₂H₅)3

Refernces

• 1、 Mochida, Kunio,Wakasa, Masanobu,Sakaguchi, Yoshio,Hayashi, Hisaharu. "Photochemical Reactions of Aryl-Substituted Digermanes through a Pair of Organogermyl Radicals". . p. 1889 - 1895. Retrieved 2007/10/02.
• 2、 Riviere, P.,Castel, A.,Satge, J.. "ASSISTANCE NUCLEOPHILE DANS DES REACTIONS D'ORGANO-HALOGENO- ET -HALOGENO-HYDROGERMANES: GERMYLANIONS, GERMYLENES, DERIVES FONCTIONNELS DU GERMANIUM". . p. 123 - 136. Retrieved 2007/10/02.