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2 article(s) from Pattison, Graham

Conformational preferences of α-fluoroketones may influence their reactivity

Graham Pattison

Beilstein J. Org. Chem. 2017, 13, 2915–2921, doi:10.3762/bjoc.13.284

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Scheme 1: Relative reactivity of α-fluoroacetophenone to α-chloroacetophenone and α-bromoacetophenone.

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Scheme 2: Competitive reduction of haloacetophenones and acetophenone.

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Figure 1: Conformational energy profiles of halogenated acetophenones (a) in gas phase; (b) in EtOH; (c) over...

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Figure 2: Optimised gas phase geometries of (a) α-fluoroacetophenone and (b) α-chloroacetophenone emphasising...

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Figure 3: Most stable conformations of (a) α-fluoroacetophenone and (b) α-chloroacetophenone in ethanol.

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Figure 4: Expected reactive conformation of halo-acetophenones.

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Figure 5: Orbital interactions in gauche- and cis-conformations of haloacetophenones.

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Figure 6: Variation of dipole moment with angle for haloacetophenones.

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Figure 7: Highest energy conformation of fluoroacetophenone, emphasizing the closeness of approach of fluorin...

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Scheme 3: Competitive reduction of fluoroacetone and chloroacetone.

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Figure 8: Conformational energy profiles of halogenated acetones in gas phase and in MeOH.

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Figure 9: Overlay of conformational energy profiles of fluoroacetone and fluoroacetophenone.

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Published 29 Dec 2017

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9,10-Dioxa-1,2-diaza-anthracene derivatives from tetrafluoropyridazine

Graham Pattison,
Graham Sandford,
Dmitrii S. Yufit,
Judith A. K. Howard,
John A. Christopher and
David D. Miller

Beilstein J. Org. Chem. 2010, 6, No. 45, doi:10.3762/bjoc.6.45

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Scheme 1: Synthesis of novel tricyclic heterocycles from pentafluoropyridine.

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Scheme 2: Synthetic route to dioxa-diaza-anthracene derivatives.

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Scheme 3: Reactions of tetrafluoropyridazine 3 with sodium phenoxide.

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Scheme 4: Synthesis of dioxa-1,2-diaza-anthracene scaffold 5.

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Scheme 5: Mechanism of formation of 5.

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Scheme 6: Reactions of dioxa-1,2-diaza-anthracene scaffold 5 with nucleophiles.

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Figure 1: Molecular structure of 4-allylamino-3-fluoro-9,10-dioxa-1,2-diaza-anthracene (9b).

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Published 06 May 2010

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