Oxidative C-H bond functionalization and ring expansion with TMSCHN2 : a copper(I)-catalyzed approach to dibenzoxepines and dibenzoazepines.

Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for the pharmaceutical industry and academic research. However, their syntheses are generally rather tedious, requiring several steps that involve a Wagner-Meerwein-type rearrangement under harsh conditions. Herein, we present the first copper(I)-catalyzed oxidative CH bond functionalization and ring expansion with TMSCHN2 to yield these important derivatives in a facile and straightforward way.

Phase behavior and molecular packing of octadecyl phenols and their methyl ethers at the air/water interface.

Noncovalent molecular interactions, such as hydrogen bonding and van der Waals forces, play an important role in self-assembling to supramolecular structures. To study these forces, we chose monolayers at the air/water interface to limit the possible arrangements of the interacting molecules. Furthermore, monolayers provide useful tools to understand and study interactions between molecules in a controlled and fundamental way.

Tetraaryl tetradecahydroporphyrazins: novel porphyrin derivatives featuring a cyclic benzene-ring tetramer.

Treatment of tetramethylsuccinonitrile 1 with aryl lithium compounds and subsequent quenching with chlorotrimethylsilane yields 5-aryl-3,3,4,4-tetramethyl-N-(trimethylsilyl)-3,4-dihydropyrrol-2-imines 2 a-c in 49-71% yield. Attempts to crystallise 2 a-c in the presence of wet air yielded the tetraaryl tetradecahydroporphyrazins 3 a-c in yields of 4-84% as single diastereomers. X-ray diffraction studies of 3 b and c showed that only the isomer with four aryl substituents pointing in the same direction was formed.