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1 article(s) from Groß, Jonathan

Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes

Savva A. Ponomarev,
Roman V. Larkovich,
Alexander S. Aldoshin,
Andrey A. Tabolin,
Sema L. Ioffe,
Jonathan Groß,
Till Opatz and
Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2021, 17, 283–292, doi:10.3762/bjoc.17.27

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Scheme 1: Scope of the nitrostyrenes 1 in the Diels–Alder reaction with CPD (dr = exo:endo).

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Figure 1: The structure assignment of norbornenes 2 by ¹H (a) and NOE (b) NMR spectroscopy.

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Figure 2: ¹³C NMR spectrum of the mixture of exo- and endo-isomers of norbornene 2l.

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Figure 3: The predicted reaction pathway for the Diels–Alder reaction of nitrostyrene 1h with CPD is displaye...

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Scheme 2: The Diels–Alder reaction of nitrostyrene 1h with spiro[2.4]hepta-4,6-diene.

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Scheme 3: Diels–Alder reaction of nitrostyrenes 1 with CHD (dr = exo:endo). (а) Reaction under microwave acti...

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Scheme 4: Kinetic study of reactions of 1h with CPD and CHD.

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Figure 4: Kinetic curves for the reactions of nitrostyrene 1h with CPD (50–130 °C) and CHD at 110 °C.

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Scheme 5: The Diels–Alder reaction of the nitrostyrene 1h with 1-methoxy-1,3-cyclohexadiene.

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Scheme 6: Selected chemical transformations of norbornenes 2 (dr = exo:endo).

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Published 27 Jan 2021

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