82265-47-2

Basic information

• Product Name: 1,1'-Binaphthalene, 8,8'-dimethoxy-
• CAS NO: 82265-47-2
• Molecular Formula: C22H18O2
• Molecular Weight: 314.384
• Mol File: 82265-47-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,1'-Binaphthalene, 8,8'-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Binaphthalene, 8,8'-dimethoxy-(82265-47-2)
• EPA Substance Registry System: 1,1'-Binaphthalene, 8,8'-dimethoxy-(82265-47-2)

Safety Data

• Hazardous Substances Data: 82265-47-2(Hazardous Substances Data)

Upstream product

• 123750-72-1 bis(1-methoxynaphthalene-8-C,O)palladium(II) 
• 87370-36-3 (N,N-dimethyl-1-naphthylamine-8-C,N)(1-methoxynaphthalene-8-C,O)palladium(II) 

Downstream Products

• 133360-71-1 C₄₄H₃₈O₂P₂ 
• 138155-68-7 7,7'-bis(3-hydroxypropyl)-8,8'-dimethoxy-1,1'-binaphthyl ditosylate 
• 138180-96-8 C₄₆H₄₂O₂P₂ 
• 133360-71-1 C₄₄H₃₈O₂P₂ 
• 133360-77-7 7,7'-bis(2-hydroxyethyl)-8,8'-dimethoxy-1,1'-binaphthyl ditosylate 

Relevant articles and documents

An unusual decarboxylative benzannulation and biaryl formation during copper(I)-promoted halogen atom transfer radical cyclization of 2-allylaryl trichloroacetates

CuCl/bpy-promoted halogen atom transfer radical cyclization of 2-allylaryl trichloroacetates in refluxing benzene gave benzannulated chloroarenes and benzannulated symmetrical biaryls along with reductive dehalogenation products. The unusual decarboxylative benzannulation and biaryl formation might be explained by a further intramolecular radical addition on the benzene ring of the eight-membered lactone intermediate, initially formed through 8-endo-trig halogen atom transfer radical cyclization, followed by decarboxylation, radical dimerization and dehydrochlorination reactions.

REACTIVITY OF CYCLOPALLADATED COMPOUNDS. VIII. SYNTHESIS OF CYCLOMETALLATED COMPOUNDS WITH AN OXYGEN AS THE DONOR ATOM. CRYSTAL AND MOLECULAR STRUCTURE OF (8-METHYLQUINOLINE-C,N)(1-METHOXYNAPHTHALENE-8-C,O)PALLADIUM(II)

Treatment of 1-methoxynaphthalene (MXNH) with n-butyllithium in a diethyl ether/n-hexane solution gives 1-methoxynaphthalene-8-lithium (MXVLi) in 30percent yield as an insoluble material.This compound reacts with PdCl2(SEt2)2 to give bis(1-methoxynaphthalene-8-C,O)palladium(II) (I) and with PtCl2(SEt2)2 to give cis- and trans-(1-methoxynaphthalene-8-C,O)(1-methoxynaphthalene-8-C)(diethylsulfide)platinum(II) (II), which are non-rigid molecules in solution.With the cyclopalladated dimers , MXNLi gives the palladobicyclic compounds: (III).An X-ray diffraction study of compound IIIa where NC = 8-methylquinoline-C,N reveals the planarity of the molecule, shows that it has a cis configuration with respect to the Pd-C bonds, and confirms that the oxygen atom of MXN is bonded to palladium: Pd-O 2.236(4) Angstroem.The geometry of IIIa is maintained in solution, whereas the corresponding compounds IIIb and IIIc in which NC is benzoquinoline-9-C,N and N,N-dimethyl-1-naphthylamine-8-C,N, respectively, appear to be mixtures of cis and trans isomers in solution.With PMe2Ph I and II give trans-Pd(MXN)2(PMe2Ph)2 and cis-Pt(MNX)2(PMe2Ph)2, respectively, in which the methoxynaphthalene is bound to the metals via the 8-carbon of the naphthalene ring.Only one phosphine ligand adds to compounds IIIb and IIIc with displacement of the OPd bond.One carbon monoxide ligand can be added to the platinum compound II to give Pt(MXN)2(SEt2)CO which in solution exists as two isomers in equilibrium.