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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.
Beilstein J. Org. Chem. 2009, 5, No. 9, doi:10.3762/bjoc.5.9
Figure 1: [2.2]Paracyclophane (1) showing standard numbering and [2.2]paracyclophane-4-thiol (2).
Scheme 1: Conversion of [2.2]paracyclophane to enantiomerically enriched [2.2]paracyclophane-4-thiol.
Scheme 2: Synthesis of [2.2](4,7)benzo[d]thiazoloparacyclophane (Rp)-10.
Beilstein J. Org. Chem. 2007, 3, No. 39, doi:10.1186/1860-5397-3-39
Scheme 1: General strategy for the synthesis of heterocycles via 5-endo-trig cyclisation
Scheme 2: Retrosynthesis of (+)-monomorine I
Scheme 3: The sulfone-mediated synthesis of 2,5-syn disubstituted pyrrolidines via a 5-endo-trig cyclisation
Scheme 4: The deprotection of N-benzoylpyrrolidines
Scheme 5: Synthesis of N-benzoyl protected pyrrolidine required for the preparation of (+)-monomorine I
Scheme 6: Mercury-mediated hydroamination
Scheme 7: Proposed transition state for mercury-mediate hydroamination
Scheme 8: Model study for the reductive amination-based cyclisation
Scheme 9: The synthesis of (+)-monomorine I