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Synthesis and conformational studies of pentahydroxy[2.1.2.1.1]‐ and hexahydroxy [2.1.1.1.1.1]metacyclophanes
Author(s) -
Yamato Takehiko,
Yasumatsu Masashi,
Doamekpor Louis Korbla,
Nagayama Souichiro
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950238
Subject(s) - chemistry , disproportionation , calixarene , condensation , cyclophane , base (topology) , formaldehyde , condensation reaction , stereochemistry , ethylene , xylene , catalysis , crystallography , molecule , organic chemistry , crystal structure , benzene , mathematical analysis , thermodynamics , physics , mathematics
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.