Stereochemistry of 1,4-Phenylenediamine-Based Bisimines:
N1,N4-dibenzylidene- and N1,N4-bis(1-phenylethylidene)benzene-1,4-diamine


Rainer Glaser* and Richard F. Murphy

Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri, 65211 (USA)


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Figure 1. Structures of 1 (R = H, left column) and 3 (R = CH3).

Figure 2. Transition state structures for the rotational enantiomerization and automerization of (E)-1 (left column) and (Z)-1.

Figure 3. Transition state structures for the rotational enantiomerization and automerization of (E)-3 (left column) and (Z)-3.

Figure 4. Transition state structures for the N-inversion of 1 (left) and 3.

Figure 5. Structures of the (E,E)-isomers of 2 (R = H, left column) and 4 (R = CH3). Cis before trans isomers and anti and syn alternate.

Figure 6. Structures of the (E,Z)-isomers of 2 (R = H, left column) and 4 (R = CH3). Cis before trans isomers and anti and syn alternate.

Figure 7. Structures of the (Z,Z)-isomers of 2 (R = H, left column) and 4 (R = CH3). Cis before trans isomers and anti and syn alternate.

Figure 8. Transition state structures for enantiomerization and automerization of (Z,Z)-2 (left) and (Z,Z)-4.

Figure 9. Transition state structures for the N-inversion of 2 (left) and 4.