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Synthesis and conformational studies of pentahydroxy[2.1.2.1.1]- and hexahydroxy [2.1.1.1.1.1]metacyclophanes

✍ Scribed by Yamato, Takehiko ;Yasumatsu, Masashi ;Doamekpor, Louis Korbla ;Nagayama, Souichiro

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 457 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199519950238

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✦ Synopsis

Abstract

Base‐catalyzed condensation of 1,2‐bis[5‐tert‐butyl‐3‐(5‐tert‐butylsalicyl)‐2‐hydroxyphenyl]ethane (8) with formaldehyde in xylene affords a novel ethylene‐bridged calixarene‐analogous macrocyclic metacyclophane. However, not the desired 2 has been obtained. Instead, the novel macrocyclic compounds pentahydroxy[2.1.2.1.1]‐ (9) and hexahydroxy‐[2.1.1.1.1.1]metacyclophane (10) have been isolated in 35 and 25% yields, respectively. The mechanism for the above disproportionation occurring during the base‐catalyzed condensation of 8 to afford these macrocyclic metacyclophanes and their ^1^H‐NMR spectral behavior are discussed.

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