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• W2069235462 abstract "Abstract Phencyclone, 1, reacted with N‐(2,6‐dimethylphenyl)maleimide, 2a; with N‐(2,6‐diethylphenyl)maleimide, 2b; and with N‐(2,6‐diisopropylphenyl)maleimide, 2c, respectively, to yield the corresponding Diels–Alder adducts, 3a–c. The adducts were extensively characterized by NMR (7 T) at ambient temperatures using one‐ and two‐dimensional (1D and 2D) proton and carbon‐13 techniques for assignments. Slow exchange limit (SEL) spectra were observed, demonstrating slow rotations on the NMR timescales, for the unsubstituted bridgehead phenyl groups [C(sp3)–C(aryl sp2) bond rotations] and for the 2,6‐dialkylphenyl groups [N(sp2)–C(aryl sp2) bond rotations]. Substantial magnetic anisotropic shifts were seen in the adducts. For example, in the N‐(2,6‐dialkylphenyl) moieties of the adducts, one of the alkyl groups is directed “into” the adduct cavity, toward the phenanthrenoid portion, and these “inner” alkyl proton NMR signals were shifted upfield. Thus, in CDCl3, the “inner” methyl of adduct 3a exhibits a proton resonance at −0.13 ppm, upfield of tetramethylsilane (TMS); the “inner” ethyl group signals from 3b appear at 0.026 ppm (CH2, quartet), and −0.21 ppm (CH3, triplet); and the “inner” isopropyl group from 3c is seen at −0.06 ppm (methine, approx. septet) and −0.39 ppm (CH3, doublet). Proton NMR of the crude N‐(2,6‐dialkylphenyl)maleamic acids (used as precursors of the maleimides, 2a–c) exhibited two sets of AB quartet signals, suggesting possible conformers from hindered rotation in the amide groups about the HN–C˭O bonds. Keywords: Dynamic NMROne‐ and two‐dimensional NMRHomonuclear and heteronuclear chemical shift correlation NMRHETCORCOSYRestricted rotation 1H and 13C NMRStereochemistryMaleimidesMaleamic acids Acknowledgments Partial support has been provided to R.R. by the U.S. Education Department (Hispanic‐Serving Institutions — Title V, and the Minority Science and Engineering Improvement Program), National Science Foundation, and the Professional Staff Congress—City University of New York Research Award Program, and to O.R. and R.T. by the Project ASCEND/McNair Program." @default.
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• W2069235462 date "2004-12-31" @default.
• W2069235462 modified "2023-10-09" @default.
• W2069235462 title "NMR Studies of Crowded Diels–Alder Adducts of Phencyclone with<i>N</i>‐(2,6‐Dialkylphenyl)maleimides. Hindered Rotations and Magnetic Anisotropy" @default.
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• W2069235462 doi "https://doi.org/10.1081/sl-120039591" @default.
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