Cyclic aryl ethers, thioethers and amines, and method for preparation.: Section Title: Heterocyclic Compounds (More Than One Hetero Atom)

Cyclic aryl ethers, thioethers or amines, and methods for synthesis are disclosed. These cyclic aryl compds. are synthesized by combining a first dinucleophile with a substituted benzene metalized electron-withdrawing complex, having halo or nitro substituent groups, to form a linear bimetalized aryl compd. The linear bimetalized aryl compd. is then reacted with a second dinucleophile to form a cyclic bimetalized aryl compd. The metalized electron-withdrawing moieties are then removed from said cyclic bimetalized aryl compd. by photolytic demetalation to form a cyclic aryl compd. I (X1, X3 = same or different and each is a alkyl, heteroalkyl, heterocyclic or arom. group having up to 6 conjugated rings, optionally substituted; X2 = benzene; n1, n3 = same or different and each is O, S, N; n4 = H, lower alkyl). Thus, reaction of 1,4-HOC6H4C6H4OH with (1,3-dichlorobenzene)(cyclopentadienyl)iron hexafluorophosphate in 1:2 molar ratio gave bimetallic ether which on further treatment with 1,4-HOC6H4C6H4OH in the presence of K2CO3 in DMF gave metalated cyclic ether; photochem. demetalation of which in CH2Cl2/MeCN gave title ether II. [on SciFinder(R)]