Preparation of cyclic aryl ethers, thioethers, and ...
|Title||Preparation of cyclic aryl ethers, thioethers, and amines.: Section Title: Heterocyclic Compounds (More Than One Hetero Atom)|
|Author(s)||A. Abd-el-Aziz, C. De Denus, L. May|
|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. having the formula I [X1, X3 = alkyl, heteroalkyl, heterocyclic or arom. group having up to 6 conjugated rings, optionally substituted; X2 = benzene; n1, n3 = O, S, N; n4 = H, lower alkyl]. E.g., reaction of 4,4'-dihydroxybiphenyl with (1,3-dichlorobenzene)cyclopentadienyliron(II) hexafluorophosphate, followed by addn. of NH4PF6, gave a bimetallic aryl ether. Photochem. demetalation of the latter led to the cyclic aryl ether. [on SciFinder(R)]|
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