TY - JOUR
T1 - Proximal O,O′-capped calix[4]arenes with a disiloxane bridge as highly efficient synthetic intermediates for 1,2-dialkylation at the lower rim
AU - Narumi, Fumitaka
AU - Morohashi, Naoya
AU - Matsumura, Nobuji
AU - Iki, Nobuhiko
AU - Kameyama, Hiroshi
AU - Miyano, Sotaro
N1 - Funding Information:
This work was supported by the Proposal-Based New Industry Creative Type Technology R & D Promotion Program from the New Energy and Industrial Technology Development Organization (NEDO) of Japan.
PY - 2002/1/21
Y1 - 2002/1/21
N2 - Treatment of calix[4]arenes with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane using imidazole as a base yielded O,O′-bridged calixarenes in excellent yields, which were subsequently treated with an alkyl halide/base to give O″,O‴-dialkylated products in high yields. These were, in turn, amenable to fluoride-promoted quantitative desilylation, thus providing an efficient method for the net proximal dialkylation of calix[4]arenes at the lower rim.
AB - Treatment of calix[4]arenes with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane using imidazole as a base yielded O,O′-bridged calixarenes in excellent yields, which were subsequently treated with an alkyl halide/base to give O″,O‴-dialkylated products in high yields. These were, in turn, amenable to fluoride-promoted quantitative desilylation, thus providing an efficient method for the net proximal dialkylation of calix[4]arenes at the lower rim.
KW - Disyloxane
KW - O,O′-bridged calix[4]arenes
KW - Proximal dialkylation
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U2 - 10.1016/S0040-4039(01)02202-X
DO - 10.1016/S0040-4039(01)02202-X
M3 - Article
AN - SCOPUS:0037147921
SN - 0040-4039
VL - 43
SP - 621
EP - 625
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 4
ER -