Cyclic aryl ethers, thioethers and amines, and ...



Title Cyclic aryl ethers, thioethers and amines, and method for preparation.: Section Title: Heterocyclic Compounds (More Than One Hetero Atom)
Author(s) Alaa S. Abd-El-Aziz, Leslie J. May, Christine R. de Denus
Start page 43
Date 2000
Abstract 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)]

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