1,6-Methano(10)annulene

1,6-Methano(10)annulene is an organic compound belonging to the class of annulenes. More specifically, it is a bridged annulene consisting of a ten-membered cyclic conjugated system (a [10]annulene) with a methylene bridge (a -CH2- group) connecting the 1 and 6 positions of the ring. This bridging significantly influences the properties of the molecule.

The presence of the methylene bridge introduces steric constraints that force the ten-membered ring into a more planar conformation compared to unsubstituted [10]annulene, which is non-planar due to steric repulsion between the internal hydrogen atoms. This enforced planarity favors π-electron delocalization around the ring, leading to enhanced aromatic character.

Synthesis of 1,6-Methano(10)annulene typically involves multi-step procedures using various organic reactions. The molecule is of interest to chemists studying aromaticity and the effects of structural modifications on the electronic properties of cyclic conjugated systems. The bridge can influence the reactivity and stability of the [10]annulene core, making 1,6-methano(10)annulene a valuable model for investigating fundamental concepts in organic chemistry.

The compound's spectroscopic properties, such as NMR spectra, are indicative of its aromatic character and the influence of the methylene bridge on the electron distribution within the conjugated system.