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Title of article :
Reductive deoxygenation of ortho-hydroxyaromatic aldehydes to 1,2-bis(hydroxyaryl)ethanes: application to the synthesis of ethylene bridged calixarene-analogous metacyclophanes
Author/Authors :
Bhatt، نويسنده , , Suchitra and Nayak، نويسنده , , Sandip K.، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2009
Pages :
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Abstract :
A novel and convenient protocol for the synthesis of hexahydroxy[]- and octahydroxy[]metacyclophanes from 4-substituted phenol in four steps has been developed. The synthetic route involved the preparation of the key intermediate 1,2-bis(5-substituted-2-hydroxyphenyl)ethanes in good yields via (i) formylation of 4-substituted phenol, (ii) reductive deoxygenation of 5-substituted 2-hydroxy aromatic aldehydes with low-valent titanium reagent and (iii) catalytic hydrogenation. The metacyclophanes were prepared by base-catalyzed macrocyclization of the above intermediates with formaldehyde in refluxing xylene in high yields.
Keywords :
ortho-Hydroxy aromatic aldehyde , 1 , McMurry coupling , Macrocyclization , 2-Bis(2-hydroxyaryl)ethanes , Metacyclophanes
Journal title :
Tetrahedron Letters
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Link To Document :