spiro[4.4]nona-1,3-diene

Base Information

• Chemical Name: spiro[4.4]nona-1,3-diene
• CAS No.: 766-29-0
• Molecular Formula: C9H12
• Molecular Weight: 120.194
• Mol file: 766-29-0.mol

Synonyms:

Chemical Property of spiro[4.4]nona-1,3-diene

Chemical Property:

• Vapor Pressure: 1.27mmHg at 25°C
• Boiling Point: 179.5°Cat760mmHg
• Flash Point: 40.5°C
• PSA: 0.00000
• Density: 0.94g/cm³
• LogP: 2.67280

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of spiro[4.4]nona-1,3-diene

There total 2 articles about spiro[4.4]nona-1,3-diene 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:

1,3,2-dioxathiepane 2,2-dioxide (5732-44-5) → bicyclo<4.3.0>nona-1(6),7-diene (24279-06-9) + spiro[4.4]nona-1,3-diene (766-29-0)

Guidance literature:

With 15-crown-5; C₅H₆Na; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 76 ℃; for 4h; Inert atmosphere;

DOI:10.1002/chem.201404515

Reference yield:

1,3,2-dioxathiepane 2,2-dioxide (5732-44-5) + sodium cyclopentadienide → bicyclo<4.3.0>nona-1(6),7-diene (24279-06-9) + spiro[4.4]nona-1,3-diene (766-29-0)

Guidance literature:

With 15-crown-5; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 76 ℃; for 4h; Inert atmosphere;

DOI:10.1002/chem.202001781

Reference yield: 85.0%

dihydridobis(acetone)bis(tris(p-fluorophenyl)phosphine)iridium(III) hexafluoroantimonate (89529-62-4) + spiro[4.4]nona-1,3-diene (766-29-0) → bis(tris(p-fluorophenyl)phosphine)(spiro[4.4]nonadiene)iridium(I) hexafluoroantimonate * 2 CH2Cl2 * (C2H5)2O

Guidance literature:

With CH₂Cl₂; (C₂H₅)2O; In neat (no solvent); freeing from air by freeze-thaw cycling; heating for 2 h at 85°C; removing the volatiles; recrystn. from CH2Cl2/Et2O; elem. anal.;

DOI:10.1021/ja00283a015

upstream raw materials:

1,3,2-dioxathiepane 2,2-dioxide

Downstream raw materials:

spiro[4.4]nonane

6-Fluoro-1,2,3,4-tetrahydro-2-naphthalene

5-<(Z)-α-Chlorbenzyliden>-endo-6-phenylspirohept-2-en-7,1'-cyclopentan>

5-<(E)-α-Chlorbenzyliden>-endo-6-phenylspirohept-2-en-7,1'-cyclopentan>

Refernces

• 1、 Wodrich, Matthew D.,Ye, Baihua,Gonthier, Jér?me F.,Corminboeuf, Clémence,Cramer, Nicolai. "Ligand-Controlled Regiodivergent Pathways of Rhodium(III)-Catalyzed Dihydroisoquinolone Synthesis: Experimental and Computational Studies of Different Cyclopentadienyl Ligands". supporting information. p. 15409 - 15418. Retrieved 2016/02/18.