The Cyclopropyl Group as a Neglected Donor in Donor–Acceptor Cyclopropane Chemistry

The Cyclopropyl Group as a Neglected Donor in Donor–Acceptor Cyclopropane Chemistry

D–A cyclopropanes bearing a simple cyclopropyl group as donor are shown to undergo a variety of [3+n]-cycloaddition reactions (n = 2–4). This behavior contrasts sharply with that of common D–A cyclopropanes with aliphatic donors. Kinetic experiments demonstrate that, in terms of donor ability, the c...

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Veröffentlicht in:Organic letters 2018-04, Vol.20 (7), p.2059-2062
Hauptverfasser: Kreft, Alexander, Jones, Peter G, Werz, Daniel B
Format: Artikel
Sprache:eng
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Zusammenfassung:D–A cyclopropanes bearing a simple cyclopropyl group as donor are shown to undergo a variety of [3+n]-cycloaddition reactions (n = 2–4). This behavior contrasts sharply with that of common D–A cyclopropanes with aliphatic donors. Kinetic experiments demonstrate that, in terms of donor ability, the cyclopropyl substituent lies between electron-rich and electron-neutral aryl donors.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00603