Doubly and Triply Bridged Polyoxapolyazaheterophanes Derived from 2,4,6-Trichloro-s-triazine

Article abstract of DOI:10.1021/jo00196a019

Doubly and triply bridged polyoxapolyazaheterophanes (1, 2) have been synthesized from 2,4,6-trichloro-s-triazine by using the different reactivity of the three chlorine atoms toward neutral nucleophiles.Introduction of alkyl groups and/or of heteroatoms in the bridging chains makes these systems soluble in organic solvents.Triazinophanes 1h and 2b, with NH groups in the bridging chains, may be used as phase-transfer catalysts in nucleophilic aliphatic substitutions. 13C NMR spectra indicate that molecules 1 and 2 either exists in a single nonsymmetric conformation up to about room temperature or, more likely, that there are two or more differently populated conformations separated by a high interconversion barrier.