Download PDF
Synthesis 1995; 1995(9): 1089-1096
DOI: 10.1055/s-1995-4075
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Selective Arylmethylation, Arylmethenylation and Aroylation of Mono- and Tetra-p-Cyanomethylcalix[4]arene

Shiv Kumar Sharma, Iftikhar Alam, C. David Gutsche*
  • *Department of Chemistry, Texas Christian University, Fort Worth, Texas 76129, USA, Fax +1(817)9217110
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Tetra-p-cyanomethylcalix[4]arene (3) is selectively converted to its tetrabenzyl ethers 4 (1,3-alternate conformer) and 1,3-dibenzyl ethers 5 (cone conformer) by reaction with benzyl halides in the presence of variable amounts of potassium carbonate. Mono-p-cyanomethylcalix[4]arene (6) gives exclusively the cone conformer of the 1,3-disubstituted product 7 (benzyl moiety attached to the unsubstituted rings). Aroylation of 6 in the presence of sodium hydride gives tetrasubstituted product 9, whereas with aluminum chloride it produces an easily separable mixture of 1,3-disubstituted compounds 10 and 11. Surprisingly, no regioselectivity is achieved using 1-methylimidazole as the base. On the other hand, 6 reacts with 4-bromobenzenesulfonyl chloride under the same reaction conditions to produce the cone conformer of the tetrasubstituted product 12. Reactions of 6 with benzyl halides or benzaldehydes using sodium hydride as a base give the fully benzylated compounds 8 or the benzal derivatives 13, respectively.

p-cyanomethylcalix[4]arene - selective arylmethylation and arylmethenylation - aroylation

      >