A Photochemical Macrocyclization Route to Asymmetric Strained [3.2] Paracyclophanes.

ABSTRACT: The intricate frameworks of paracyclophanes are an important target for synthesis since they are found in various chiral auxiliaries, solar cells, high-performance plastics, pharmaceuticals, and molecular machines. Whereas numerous methods exist for the preparation of symmetric paracyclophanes, protocols for the efficient synthesis of strained asymmetric scaffolds are limited. Here we report a remarkably simple photochemical route to strained [3.2]paracyclophanes starting from readily available educts. By way of NMR and X-ray analyses, we discovered that UV-irradiation of an aromatic carboxylic ester tethered to a toluene moiety leads to the intramolecular formation of a new C-C bond, with loss of an alcohol. A systematic evaluation of the reaction conditions and substituents, as well as r

SUBMITTER: Haensch VG 

PROVIDER: S-EPMC10092696 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature