121617-88-7

Basic information

• Product Name: exo-(4-phenyl-9,10-dihydrophenanthreno)-2':3',9:10-norbornane
• Synonyms: exo-(4-phenyl-9,10-dihydrophenanthreno)-2':3',9:10-norbornane
• CAS NO: 121617-88-7
• Molecular Weight: 322.45
• Mol File: 121617-88-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: exo-(4-phenyl-9,10-dihydrophenanthreno)-2':3',9:10-norbornane(CAS DataBase Reference)
• NIST Chemistry Reference: exo-(4-phenyl-9,10-dihydrophenanthreno)-2':3',9:10-norbornane(121617-88-7)
• EPA Substance Registry System: exo-(4-phenyl-9,10-dihydrophenanthreno)-2':3',9:10-norbornane(121617-88-7)

Safety Data

• Hazardous Substances Data: 121617-88-7(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 498-66-8 norbornene 
• 498-66-8 norborn-2-ene 
• 108-86-1 bromobenzene 

Downstream Products

• 121617-91-2 4-phenylphenanthreno-2',3':9,10-norbornene 

Relevant articles and documents

Palladium-catalyzed domino coupling reactions of aryl halides with norbornene and norbornene derivatives - A simple route to polycyclic aromatic compounds

Under palladium-catalysis, norbornene 1, dicyclopentadiene 10, norbornenol 13, and norbornenone 15 react with unsubstituted as well as substituted bromo- and iodobenzenes to give 1 : 3 coupling products with 4-aryl-9,10-dihydrophenanthrene units with up to 70% isolated yields. The structures of two such products 4a and 4e were proved by X-ray crystal structure analysis. 2-Bromothiophene 17 reacts with 1 and 10 to yield a mixture of 2 : 1 and 3 : 1 coupling products, while 3-iodopyridine 22a, 3-iodo-6-methylpyridine 22b and 4-iodopyridine 25 give only 2 : 1 coupling products with 5,6-dihydro-3,8-phenanthroline and 5,6-dihydro-2,9-phenanthroline units, respectively. Some new mechanistic insights into this interesting four-component domino coupling reaction are presented. The products can easily be transformed by photocyclization/dehydrogenation and/or flash vacuum pyrolysis to a variety of cyclopentadiene-anellated polycyclic aromatic compounds in very high yields. The reported sequence also presents the easiest access to benzo[e]pyrene.

Selektive 1:3-Kupplung von Norbornen und Iodbenzol; einfache Synthese Cycloaliphaten-anellierter Benzopyrene

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