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Diester intrabridging of p-tert-butylcalix[8]arene and unexpected formation of the monospirodienone derivative

✍ Scribed by Grazia M.L Consoli; Corrada Geraci; Francesca Cunsolo; Placido Neri

Book ID: 104252596
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 101 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02485-1

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✦ Synopsis

Reaction of p-tert-butylcalix[8]

arene 1 with adipoyl chloride in the presence of NaH as the base yielded singly and doubly intrabridged esters 2-4 and 6. Surprisingly, calix[8]arene monospirodienone derivative 7 was also isolated, which was originated by O 2 oxidation. The conditions of this oxidation were optimized leading to a novel synthetic approach to calixarene monospirodienones based on the O 2 /NaH/acyl-chloride oxidizing system. Xantheno calix[8]arenes 8-8a were obtained by rearrangement of 7.

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