Peri-naphthalenes

In organic chemistry, peri-naphthalenes are particular derivatives of naphthalene with the formula C10H6-1,8-X2.

Owing to the rigidity of the naphthalene skeleton, these substituents on the 1- and 8-positions are constrained to be relatively close 2.5 Å, which is within the van der Waals radius for many atoms.

In contrast, ortho-substituents pendant from a benzene ring are separated by about 3.3 Å.

Other distinctive compounds include the diphosphine 1,8-bis(diphenylphosphino)naphthalene (dppn) and the disulfide, both of which are ligand precursors.

[3] Certain perinaphthalene derivatives can be prepared from 1,8-dilithionaphthalene, which in turn is generated by dilithiation of 1-bromonaphthalene:[4] The deprotonation requires TMEDA.

General structure of a perinaphthalene, where R1 and R2 represent the substituents.
Four peri-naphthalene derivatives.