74498-50-3

Upstream product

• 10029-00-2 4-acetyl[2.2]paracyclophane 
• 43044-95-7 pseudogem-Acetyl(chloromethyl)<2.2>paracyclophane 
• 43045-00-7 pseudogem-Bis(bromomethyl)<2.2>paracyclophane 
• 74498-49-0 pseudogem-Aldehydocarboxy<2.2>paracyclophane 
• 43044-98-0 pseudogem-Bis(hydroxymethyl)<2.2>paracyclophane 
• 1633-22-3 [2.2]Paracyclophan 

Relevant academic research and scientific papers

Synthesis, structure, and first reactions of a new class of thiacyclophanes?

In our effort to prepare [m.n]cyclophanes carrying functional groups in their molecular bridges, the thiacyclophanes 14, 19, 20, and 21 have been prepared by simple routes from the pseudo-gem dibromide 10a and the corresponding bis-thiol 10b. The triply-bridged bis-thia-cyclophanes 14, and 19-21 were characterized by their spectroscopic data as well as by X-ray structural analyses. The meta-isomer 20 was oxidized to the bis-sulfone 23, which on flash vacuum pyrolysis (FVP) yielded a product mixture presumably containing the hydrocarbon 26 with a cleaved molecular bridge. Subjecting 23 to Ramberg-B?cklund conditions (CCl4, NaOH, phase transfer catalysis) provided the chloride 24 in poor yield (9%), a [2.2]paracyclophane in which the new molecular bridge is fully conjugated.

Macro Rings. 49. Use of Transannular Reactions to Add Bridges to Paracyclophane

New transannular reactions were used to introduce additional bridges into paracyclophane (1).With CH2O-HCl, 4-acetylparacyclophane (3) gave (55percent) 4-acetyl-13-(chloromethyl)paracyclophane (4), whose substituents are pseudogem to one an