Discovery of a Long-Range Perlin Effect in a Conformationally Constrained Oxocane
Herein, we present the crystal structure, NMR J analysis, and conformational and natural bond order analyses of tricyclic oxocane (1), resulting in the discovery of a long-range Perlin effect at C4 and C5. The normal Perlin effect (NPE) of Δ1JC–H = 18.38 Hz at C5 is the largest to date for a nonanomeric methylene due to an unprecedented through-space n → σ* stabilizing interaction. The NPE at C4 where Δ1JC–H = 6.91 Hz is nearly double those found in cyclohexanone.
This article is cited by 3 publications.
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- Kahlil S. Salome, Cláudio F. Tormena. Revisiting the Long-Range Perlin Effect in a Conformationally Constrained Oxocane. The Journal of Organic Chemistry 2018, 83 (17) , 10501-10504. https://doi.org/10.1021/acs.joc.8b00935
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