Cyclic Aryl Ethers, Thioethers and Amines, and Method for Preparation

Cyclic aryl ethers, thioethers or amines, and methods for synthesis are
disclosed. These cyclic aryl compounds are synthesized by combining a first
dinucleophile with a substituted benzene metallized electron-withdrawing
complex,
having halo or nitro substituent groups, to form a linear bimetallized aryl
compound. The linear bimetallized aryl compound is then reacted with a second
dinucleophile to form a cyclic bimetallized aryl compound. The metallized
electron-withdrawing moieties are then removed from said cyclic bimetallized
aryl
compound by photolytic demetallation to form a cyclic aryl compound having the
formula

Image

wherein:
X1 and X3 are the same or different and each is a alkyl, heteroalkyl,
heterocyclic or aromatic group having up to 6 conjugated rings, optionally
substituted;
X2 is benzene
n1 and n3 are the same or different and each is O, S or N; and
n4 is H or lower alkyl.