4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene

Base Information

• Chemical Name: 4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene
• CAS No.: 799278-90-3
• Molecular Formula: C₃₀H₃₄Sn
• Molecular Weight: 513.31
• Mol file: 799278-90-3.mol

Synonyms:

Chemical Property of 4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene

There total 1 articles about 4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene 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: 92.0%

3-(triphenylstannyl)propyl 4-methylbenzenesulfonate (799278-89-0) + 1-tert-butyl-1,3-cyclopentadiene (84857-63-6) → 1,4-di-tert-butyltricyclo[5.2.1.0(1,7)]deca-3,8-diene + 4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene (799278-90-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; paraffin; under exclusion of moisture and air; t-BuCpH added dropwise to NaH suspn. in paraffin at -78°C; warmed to room temp. under stirring; cooled to -78°C; soln. of Sn compd. in THF added dropwise; warmed to room temp. for 12 h; volatiles removed; sepd. by chromy. (SiO2, gradient petroleum ether-ethyle acetate 5:1, 1:1);

DOI:10.1016/j.jorganchem.2004.06.065

Reference yield: 47.0%

4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene (799278-90-3) + iron(II) chloride → bis[η5-1-(tert-butyl)-3-(3-triphenylstannylpropyl)cyclopentadienyl]iron(II) (799278-93-6)

Guidance literature:

With phenyllithium; In tetrahydrofuran; diethyl ether; cyclohexane; under exclusion of moisture and air; PhLi (1.2 equiv.) in cyclohexane-Et2O added dropwise at 0°C to soln. of Sn compd. in THF; stirred atroom temp. for 15 min; FeCl2 (0.5 equiv.) added; stirred for 3 h; acidified with 20% citric acid-H2O (ice-cooling); aq. layer extd. with CH2Cl2; combined org. layers dried (MgSO4); concd.; chromd. (SiO2, petroleum ether-EtOAc 20:1); isolated from second fraction; elem. anal.;

DOI:10.1016/j.jorganchem.2004.06.065

Reference yield: 39.0%

zirconium tetrachloride bis(tetrahydrofuran) complex (21959-01-3,125410-70-0,125410-71-1) + 4-(tert-butyl)-1-(3-triphenylstannylpropyl)-1,3-cyclopentadiene (799278-90-3) → bis[η5-1-(tert-butyl)-3-(3-triphenylstannylpropyl)cyclopentadienyl]dichlorozirconium(IV) (799278-95-8)

Guidance literature:

With phenyllithium; In tetrahydrofuran; diethyl ether; cyclohexane; PhLi (1 equiv.) in cyclohexane-Et2O added dropwise to soln. of Sn compd.in THF at -78°C; stirred for 15 min; soln. of Zr salt (0.5 equiv .) in THF added dropwise at -78°C; warmed to room temp. for 16 h; volatiles removed; extd. with boiling toluene; concd.;

DOI:10.1016/j.jorganchem.2004.06.065

upstream raw materials:

3-(triphenylstannyl)propyl 4-methylbenzenesulfonate

1-tert-butyl-1,3-cyclopentadiene

Downstream raw materials:

bis[η5-1-(tert-butyl)-3-(3-triphenylstannylpropyl)cyclopentadienyl]dichlorozirconium(IV)

bis[η5-1-(tert-butyl)-3-(3-triphenylstannylpropyl)cyclopentadienyl]iron(II)

bis[η5-1-(tert-butyl)-3-(3-tributylstannylpropyl)cyclopentadienyl]iron(II)