Transformation of two-dimensional structures of noncyclic isobutenyl diamide compounds by tandem Claisen rearrangement

Two-dimensional structure of an isobutenyl diamide compound containing ether moieties was investigated by scanning tunneling microscopy at solid/liquid interface. The naphthalene units of the compound aligned in a wavy arrangement. The compound was modified by tandem Claisen rearrangement (TCR), which resulted in the transformation of the ether functions into hydroxyl group and in the formation of a C-C bond. Due to the alteration of the molecular structure, the two-dimensional structure changed from wavy to straight arrangements. In other words, drastic transformation of self-assembled structures could be achieved by the "simple" one-pot thermal reaction of TCR. (C) 2010 Elsevier B.V. All rights reserved.