24262-20-2

Basic information

• Product Name: 1,4(1,4)-dibenzenacyclohexaphane-1²,4³-diol
• CAS NO: 24262-20-2
• Molecular Weight: 240.302
• Mol File: 24262-20-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,4(1,4)-dibenzenacyclohexaphane-1²,4³-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4(1,4)-dibenzenacyclohexaphane-1²,4³-diol(24262-20-2)
• EPA Substance Registry System: 1,4(1,4)-dibenzenacyclohexaphane-1²,4³-diol(24262-20-2)

Safety Data

• Hazardous Substances Data: 24262-20-2(Hazardous Substances Data)

Upstream product

• 1633-22-3 [2.2]Paracyclophan 
• 301817-11-8 4,12-bis(formyl)[2.2]paracyclophane 
• 36325-27-6 4-formyl[2.2]paracyclophane 
• 383191-69-3 4,12-dihydroxy-5,13-dipentanoyl[2.2]paracyclophane 
• 196316-30-0 4,16-dibromo[2.2]paracyclophane 

Downstream Products

• 612492-27-0 (R)-(+)-4,12-dihydroxy[2.2]paracyclophane 
• 612492-27-0 (S)-(-)-4,12-dihydroxy[2.2]paracyclophane 
• 157018-15-0 (R_p)-(+)-4-hydroxy-[2.2]paracyclophane 
• 5628-11-5 4-hydroxy-[2,2]-paracyclophane 
• 612492-27-0 (S_p)-(-)-4,12-dihydroxy-[2.2]paracyclophane 
• 612492-27-0 (R_p)-4,12-dihydroxy[2.2]paracyclophane 

Relevant articles and documents

A curious benzenoid deacylation reaction: Neighbouring group participation in acylhydroxy[2.2]paracyclophanes

Attempted carbonyl reduction of acyldihydroxy[2.2]paracyclophanes with sodium borohydride led instead to competing aromatic deacylation. The effect was traced to a neighbouring group participation that can be correlated with carbonyl IR stretching frequencies. Deuterium labelling studies implicate the formal intermediacy of a solvated [2.2]paracyclophane anion via an SE1 mechanism.

Highly Efficient Kinetic Resolution of PHANOL by Chiral Phosphoric Acid Catalyzed Asymmetric Acylation

We report herein a highly efficient kinetic resolution of PHANOL by chiral phosphoric acid catalyzed asymmetric acylation. PHANOL enantiomers were well differentiated by the chiral environment of chiral phosphoric acid, and both the corresponding monoester and PHANOL were obtained with excellent enantioselectivities (98% ee and 92% ee, respectively). Detailed examination of the substrates suggests that the presence of two hydroxy groups in PHANOL was critical for both reactivity and enantioselectivity.

Synthesis, chiral resolution, and absolute configuration of dissymmetric 4,12-difunctionalized [2.2]paracyclophanes

Racemic 4,12-difunctionalized [2.2]paracyclophanes were synthesized and successfully resolved by (recycling) HPLC on a stationary CHIRALPAK IA phase at a semipreparative scale. Their absolute configurations were determined by X-ray crystal structure analy