Biphenol diamine

Biphenol diamine PMDA polyetherimide (8.9) Aurum Mitsui Toatsu Chemical Co. 

Figure 7.3 Chemical structure of biphenol diamine PMDA polyetherimide (Aurum , Vespel TP-8000 series).

N,N -Dimethyl-1,2-diphenylethylenediamine and related chiral diamines are not only useful chiral auxiliaries in asymmetric synthesis, but they have also found applications as analytical reagents. They allow the resolution and the determination of enantiomeric composition of aldehydes by formation of diastereomeric aminals.31 34 Combined with PCI3, they allow determination of the enantiomeric composition of alcohols, biphenols, thiols and amines.35 36 The diamine described here is used most extensively. 

Figure 15.6 Reaction of hindered biphenols with a diamine [41].

So far we have seen the reactions of chlorocyclophosphazenes with reagents that may be termed monofunctional. For example, a phenol in its reactions with chlorocyclophosphazenes will react as a nucleophile and form N3P3(OPh)6 containing P-0 linkages. If instead of a phenol we used a biphenol we will have two sites that can react with the phosphorus centers. In this manner there are several difunctional reagents such as diamines (ethylenediamine, 1,3-diaminopropane, phenylenediamine), diols (ethyleneglycol, 1,3-propanediol, catechol), and amino alcohols (ethanolamine, propanolamine, o-aminophenol) [2,15]. 

Figure 9 ICD spectra of complexes between bisphenol host 11 (6.83 X 10 M) and chiral diamine guest 12 (1.37 x 10 M). (Reprinted from Tetrahedron Lett., 38, T. Mizutani, H. Takagi, O. Kara, et ah, Axial chirality induction in flexible biphenols by hydrogen bonding and steric interactions, 1991, Cop)night (1997), with permission from Elsevier.)...

By condensation of a biphenol with 2-fluoro-5-nitrobenzenesulfonic acid sodium salt [79,80] or 5-amino-2-chlorobenzenesulfonic acid [81], some sulfonated diamines bearing the siflfonic group on the terminal amino phenyl ring can be synthesized (Fig. 8). 

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