Exocyclic and in-ring alkene-containing calix[4]arenes via reaction of a 2-(iodomethyl)calix[4]arene

ORGN 762

Jordan L. Fantini, fantinij@denison.edu1, Michael J. Kahlenberg, kahlen_m@denison.edu1, Kenneth P. Klatt1, and Lara R. Liou, lrk22@cornell.edu2. (1) Department of Chemistry and Biochemistry, Denison University, Ebaugh Laboratories, Granville, OH 43023, (2) Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14850
Tetramethoxy-p-tert-butylcalix[4]arene reacts with butyl lithium and diiodomethane to afford the versatile precursor 2-(iodomethyl)-tetramethoxy-p-tert-butylcalix[4]arene. This compound undergoes dehydroiodination with KOH to yield the exocyclic alkene compound 2-methylene-tetramethoxy-p-tert-butylcalix[4]arene. In the absence of base, rearrangement takes place with dehydroiodination to give a ring-expanded alkene-containing calixarene. These two compounds have been characterized by various methods including single crystal x-ray diffraction. The reactivity and conformational behavior of these compounds will be described.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006