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Beilstein J. Org. Chem. 2021, 17, 1518–1526, doi:10.3762/bjoc.17.109
Graphical Abstract
Figure 1: The common [2.2]cyclophanes.
Scheme 1: Nitration of [2.2]paracyclophane (1) and the synthesis of 4-hydroxy-5-nitro[2.2]metaparacyclophane (...
Figure 2: Crystal structure of 5. Ellipsoids are drawn at a 50% probability level [63-66].
Figure 3: Crystal structure of 6. Ellipsoids are drawn at a 50% probability level [63].
Scheme 2: Possible mechanism for the formation of [2.2]metaparacyclophane 5 and cyclohexadienone cyclophane 6...
Scheme 3: Conjugate addition of methanol and subsequent elimination.
Figure 4: Crystal structure of 14. Ellipsoids are drawn at a 50% probability level [63].
Figure 5: Crystal structure of 15. Ellipsoids are drawn at a 50% probability level [63].
Figure 6: Possible origin of stereoselectivity.