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3 article(s) from Tantillo, Dean J

Correction: Dynamic behavior of rearranging carbocations – implications for terpene biosynthesis

Stephanie R. Hare and
Dean J. Tantillo

Beilstein J. Org. Chem. 2017, 13, 1669–1669, doi:10.3762/bjoc.13.161

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Figure 1: Corrected Figure 6 of the original article. The portion of the norborn-2-en-7-ylmethyl cation PES e...

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Original
Article

Correction

Published 15 Aug 2017

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Dynamic behavior of rearranging carbocations – implications for terpene biosynthesis

Stephanie R. Hare and
Dean J. Tantillo

Beilstein J. Org. Chem. 2016, 12, 377–390, doi:10.3762/bjoc.12.41

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Graphical Abstract

Figure 1: Representative terpenes.

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Figure 2: Two different models showing how energy evolves throughout the course of a reaction: (a) a two-dime...

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Figure 3: A depiction of the “snowboarder” analogy for reactions displaying non-statistical dynamic effects. ...

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Figure 4: The tetramethylbromonium ion system [14].

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Figure 5: The reaction mechanisms of interest in the PES and dynamics studies of Dupuis and co-workers (R = CH...

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Figure 6: The portion of the norborn-2-en-7-ylmethyl cation PES examined by Ghigo et al. [60]. Energies reported ...

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Figure 7: The transformation of 2-norbornyl cation to 1,3-dimethylcyclopentyl cation.

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Figure 8: Carbocation rearrangements for which trajectory calculations were used to estimate lifetimes of sec...

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Figure 9: Carbocation rearrangements involved in abietadiene formation.

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Figure 10: Carbocation rearrangements involved in miltiradiene formation.

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Figure 11: Top: carbocation rearrangements involved in epi-isozizaene formation. Bottom: reaction coordinate d...

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Correction

Review

Published 29 Feb 2016

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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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Full Research Paper

Published 13 Feb 2013

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