1227781-48-7

Basic information

• Product Name: (rac)-4-azido[2.2]paracyclophane
• Synonyms: (rac)-4-azido[2.2]paracyclophane
• CAS NO: 1227781-48-7
• Molecular Weight: 249.315
• Mol File: 1227781-48-7.mol

Chemical Properties

• CAS DataBase Reference: (rac)-4-azido[2.2]paracyclophane(CAS DataBase Reference)
• NIST Chemistry Reference: (rac)-4-azido[2.2]paracyclophane(1227781-48-7)
• EPA Substance Registry System: (rac)-4-azido[2.2]paracyclophane(1227781-48-7)

Safety Data

• Hazardous Substances Data: 1227781-48-7(Hazardous Substances Data)

Downstream Products

• 141083-01-4 N-benzoyl-4-amino<2.2>paracyclophane 
• 10122-95-9 (R_p)-1,4(1,4)-dibenzenacyclohexaphan-1²-amine 
• 10122-95-9 (S_p)-4-amino[2.2]paracyclophane 
• 1453841-14-9 1-([2.2]paracyclophan-4-yl)-4-phenyl-1H-1,2,3-triazole 
• 1453841-16-1 5-(diphenylphosphino)-1-([2.2]paracyclophan-4-yl)-4-phenyl-1H-1,2,3-triazole 
• 1453841-18-3 5-(dicyclohexylphosphino)-1-([2.2]paracyclophan-4-yl)-4-pentyl-1H-1,2,3-triazole 
• 1453841-17-2 5-(diphenylphosphino)-1-([2.2]paracyclophan-4-yl)-4-pentyl-1H-1,2,3-triazole 
• 1430616-73-1 C₇₂H₆₀Cl₂N₆P₂Pd 
• 1430723-27-5 tris(1-(tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaen-5-yl)-5-phenyltriazol-4-yl)phosphine 
• 1430616-68-4 diphenyl(1-(tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaen-5-yl)-5-phenyltriazol-4-yl)phosphine 
• 1430616-64-0 1-(tricyclo[8.2.2.2(4,7)]hexadeca-4,6,10,12,13,15-hexaen-5-yl)-5-phenyltriazole 
• 123439-12-3 4-amino[2.2]paracyclophane 
• 1227781-56-7 C₃₁H₃₉N₂PSe 
• 1227781-55-6 C₃₁H₃₉N₂OP 

Relevant articles and documents

Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts

For the first time it is shown that exceptionally electron-rich arene rings can be fluorinated exclusively during the reductive elimination reactions of diaryliodonium fluorides. The 5-methoxy[2.2]paracyclophan-4-yl directing group simultaneously reduces unproductive aryne chemistry and eliminates ligand exchange reactions by a combination of steric and electronic effects. Use of the cyclophane directing group permits an unprecedented degree of control in fluorination reactions of diaryliodonium salts.

Iodonium Cyclophanes for SECURE Arene Functionalization

This disclosure relates to compounds, reagents, and methods useful in the synthesis of aryl fluorides, for example, in the preparation of 18F labeled radiotracers. For example, this disclosure provides universal “locked” aryl substituents that result in StereoElectronic Control of Unidirectional Reductive Elimination (SECURE) from diaryliodonium salts. The reagents and methods provided herein may be used to access a broad range of compounds, including aromatic compounds, heteroaromatic compounds, amino acids, nucleotides, and synthetic compounds.

Regiospecific reductive elimination from diaryliodonium salts

(Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.