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- Title
Functionalization of the periphery of calix[4]resorcinarenes with P(III)-containing substituents via hydroxy, trimethylsiloxy, and ethoxy-tethered trimethylsiloxy intermediates.
- Authors
Neda, Ion; Vollbrecht, Alexander; Grunenberg, Jörg; Schmutzler, Reinhard
- Abstract
Unlike C-undecylcalix[4]resorcinarene, C-methylcalix[4]resorcinarene 1 reacted with chlorodifluorophosphine in the absence of an auxiliary base to give the unstable octakis(difluorophosphite)-substituted derivative 2. The existence of two conformational isomers of 2 in solution was observed by 19F and 31P NMR spectroscopy. Attempts to react the octakis(trimethylsilyl)calix[4]resorcinarene 3 and its tetrabromo derivative 4 with phosphorus trichloride and chlorodifluorophosphine were unsuccessful. The ethoxy-tethered C-methyl-octakis(trimeth-ylsilyl)calix[4]resorcinarene 5 was allowed to react with 2-chloro-1,3,5-trimethyl-1,3,5-triaza-2σ3λ3-phosphorin-4,6-dione and chlorodifluorophosphine. By substitution of all trimethylsilyl groups, the octakis(phosphorus(III))-substituted compounds 6 and 7 were formed. As for 2, dynamic behavior in solution was observed for 6 and 7, arising from the equilibrium between different conformational isomers. © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9:553-558, 1998
- Publication
Heteroatom Chemistry, 1998, Vol 9, Issue 6, p553
- ISSN
1042-7163
- Publication type
Article
- DOI
10.1002/(SICI)1098-1071(1998)9:6<553::AID-HC5>3.0.CO;2-5