(1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene

Base Information

• Chemical Name: (1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene
• CAS No.: 31641-96-0
• Molecular Formula: C₁₃H₁₄
• Molecular Weight: 170.254
• Mol file: 31641-96-0.mol

Synonyms:(1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene

Chemical Property of (1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene

There total 4 articles about (1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene 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: 81.0%

norborn-2-ene (498-66-8) + bromobenzene (108-86-1,52753-63-6) → 2-phenylnorborn-2-ene (4237-08-5) + (1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene (31641-96-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium salt of di-t-butyl-p-cresol; In various solvent(s); at 105 ℃; Yields of byproduct given;

DOI:10.1016/0022-328X(85)80360-0

Reference yield: 65.0%

norborn-2-ene (498-66-8) + bromobenzene (108-86-1,52753-63-6) → biphenyl (92-52-4,1594-86-1) + (1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene (31641-96-0) + (2RS,15SR)-pentacyclo[14.2.1.02,15.03,8.09,14]nonadeca-3(8),4,6,9(14),10,12-hexaene

Guidance literature:

With potassium tert-butylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In various solvent(s); at 105 ℃; for 24h; Product distribution; further aromatic bromides, base and products;

Reference yield:

norborn-2-ene (498-66-8) + bromobenzene (108-86-1,52753-63-6) → (1α,4α,4aβ,8bβ)-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylene (31641-96-0) + C26H28

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; at 105 ℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1055/s-1996-4286

upstream raw materials:

norborn-2-ene

bromobenzene

iodobenzene

Refernces

• 1、 Catellani, Marta,Chiusoli, Gian Paolo,Ricotti, Stefano,Sabini, Fabrizio. "PALLADIUM-CATALYZED C-C BOND FORMATION INVOLVING AROMATIC C-H ACTIVATION. IV. NEW SYNTHETIC APPLICATIONS OF INSERTION REACTIONS COUPLED WITH INTRAMOLECULAR AROMATIC SUBSTITUTION". . p. 685 - 690. Retrieved 2007/10/02.