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1 article(s) from Nguyen, Quynh Nhu N

Caryolene-forming carbocation rearrangements

Quynh Nhu N. Nguyen and
Dean J. Tantillo

Beilstein J. Org. Chem. 2013, 9, 323–331, doi:10.3762/bjoc.9.37

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Graphical Abstract

Figure 1: Caryol-1(11)-en-10-ol (1) and similar sesquiterpenoids. Note that a different atom numbering was us...

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Scheme 1: Initially proposed mechanism for caryolene (caryol-1(11)-en-10-ol, 1) formation. Atom numbers for f...

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Figure 2: Computed (top) and experimental (bottom, underlined italics) [2] ¹H and ¹³C chemical shifts for 1 (low...

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Figure 3: Computed minima and transition-state structure involved in the single-step conversion of A to C. Re...

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Figure 4: IRC from TS-AC toward C. Relative energies were calculated at the B3LYP/6-31+G(d,p) level.

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Scheme 2: Alternative mechanisms for caryolene formation.

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Figure 5: Computed pathway for the conversion of C to E. Relative energies shown (kcal/mol) were calculated a...

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Figure 6: IRC from TS-GE toward E. Relative energies were calculated at the B3LYP/6-31+G(d,p) level. Selected...

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Figure 7: Computed pathway for the conversion of C to E in the presence of ammonia. Relative energies shown (...

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Figure 8: Predicted energetics for the conversion of A to E in the absence (blue) and presence (auburn) of am...

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Published 13 Feb 2013

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