Switching Selectivity in  o ‐Benzoquinone Cycloadditions | Zendy

AlTalib Mahmoud | Zendy; Gerstenberger Ina | Zendy; Jones Peter G. | Zendy; Winterfeldt Ekkehard | Zendy

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Switching Selectivity in o ‐Benzoquinone Cycloadditions

Author(s) -

AlTalib Mahmoud,

Gerstenberger Ina,

Jones Peter G.,

Winterfeldt Ekkehard

Publication year - 1997

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199719970517

Subject(s) - chemistry , regioselectivity , cyclopentadiene , chemoselectivity , selectivity , adduct , benzoquinone , derivative (finance) , cycloaddition , medicinal chemistry , 1,4 benzoquinone , organic chemistry , quinone , catalysis , financial economics , economics

Whereas m ‐methoxy‐ o ‐benzoquinone 6 , like other unsaturated ketones, operates as a dienophile in Diels–Alder cycloadditions, the corresponding methyl derivative 7a behaves as an electron‐poor 4π‐system under exactly the same conditions. With the nonsymmetric cyclopentadiene 2 (X = MeO), adduct 9a is formed with excellent chemoselectivity, face‐selectivity, and regioselectivity.

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