TY - JOUR
T1 - Conversion of mono- and tetra-thiacalix[4]arenes to sulfilimine derivatives and unexpected formation of monospirodienone derivatives
AU - Morohashi, Naoya
AU - Kojima, Makoto
AU - Suzuki, Akihiro
AU - Ohba, Yoshihiro
N1 - Funding Information:
The authors wish to thank Dr. A. Fujimori, Mr. N. Suto, and Mr. R. Masuya, Yamagata University, for their kind assistance in measuring X-ray reflection intensity. This work was supported by a Grant-in-Aid for Scientific Research from Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 15750111).
PY - 2005
Y1 - 2005
N2 - The treatment of mono- and tetra-thiacalix[4]arenes (2, 3) with chloramine T gave unexpected monospirodienone derivatives (4, 5). The reaction of methyl ethers (6, 7) of thiacalix[4]arenes with chloramine T followed by demethylation gave novel derivatives (10, 11) having a sulfilimine group. X-ray analysis revealed that 11 adopts cone conformation in the solid state, in which the sulfilimine group directs toward axial orientation to take part in circular hydrogen bonding with four OH groups.
AB - The treatment of mono- and tetra-thiacalix[4]arenes (2, 3) with chloramine T gave unexpected monospirodienone derivatives (4, 5). The reaction of methyl ethers (6, 7) of thiacalix[4]arenes with chloramine T followed by demethylation gave novel derivatives (10, 11) having a sulfilimine group. X-ray analysis revealed that 11 adopts cone conformation in the solid state, in which the sulfilimine group directs toward axial orientation to take part in circular hydrogen bonding with four OH groups.
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U2 - 10.1515/HC.2005.11.3-4.249
DO - 10.1515/HC.2005.11.3-4.249
M3 - Article
AN - SCOPUS:23644439903
SN - 0793-0283
VL - 11
SP - 249
EP - 254
JO - Heterocyclic Communications
JF - Heterocyclic Communications
IS - 3-4
ER -