Calixarenes. II. The isolation and characterization of the calix[4]arene and the bishomooxacalix[4]arene from A p-t-butylphenol-formaldehyde condensation product

✍ Scribed by C.David Gutsche; Ramamurthi Muthukrishnan; Kwang Hyun No

• Book ID: 104244763
• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 236 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93679-2

✦ Synopsis

Sw/onary. The base-catalyzed condensation of p-t-butylphenol and formaldehyde, which yields a cyclic octamer (I, n-8) as the major product, has been shown to also yield a cyclic tetramer (I, n=4) and a bishomoo~a cyclic tetramer (II). The base-catalyzed reaction of p-substituted phenols and formaldehyde yields cone-shaped cyclic oligomers (I) to which the name culixarene has been assigned'. These compounds are of interest because of their ability to form complexes and, when appropriately functionalized, to be enzyme model candidates. The product from p-t-butylphenol and formaldehyde, originally assigned a cyclic tetrameric structure (I, n=4)', has recently been shown to be a mixture of materials' in which the major component is the calix[8]arene (I, n=8) accompanied by a small amount of a second material thought to be the calix[5]arene or calix[6]arene. It has now been discovered that when the reaction conditions are slightly changed also be isolated, and these are shown to be the calix[4]arene (I, calix[4]arene (II).