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Laali, K.K.* ; Okazaki, T.* ; Bunge, S.D.* ; Lenoir, D.

Stable ion and electrophilic chemistry of the sterically crowded stilbene 1,1'-Bi(benzocyclobutenylidene) and its derivatives.

J. Org. Chem. 73, 4092-4100 (2008)
DOI
Open Access Green möglich sobald Postprint bei der ZB eingereicht worden ist.
Generation and NMR studies of novel carbocations and carboxonium ions are reported from sterically hindered stilbene 1,1'-bi(benzocyclobutenylidene) 1, its dimethoxy derivative 5, and from their skeletally rearranged derivatives, namely, the spirocyclic ketone 6, diastereomeric alcohols 7 and isomeric diols 8. Quenching experiments on the carbocations under various conditions resulted in the formation/isolation of several novel covalent adducts. Acid-catalyzed isomerization of the diols 8 produced a remarkable dimeric molecule, whose structure was confirmed by X-ray analysis. Reactions of hindered stilbenes 1 and 5 with Br 2/CDCl 3 were examined via NMR experiments. The experimentally observed carbocations were also studied computationally by GIAO-DFT and by NICS.
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Publikationstyp Artikel: Journalartikel
Dokumenttyp Wissenschaftlicher Artikel
Schlagwörter 1;1'-bi(benzocyclobutenylidene); Acid-catalyzed isomerization; McMurry coupling; Electrophilic bromination
Sprache englisch
Veröffentlichungsjahr 2008
HGF-Berichtsjahr 2008
ISSN (print) / ISBN 0022-3263
e-ISSN 1520-6904
Quellenangaben Band: 73, Heft: 11, Seiten: 4092-4100 Artikelnummer: , Supplement: ,
Verlag American Chemical Society (ACS)
Begutachtungsstatus Peer reviewed
Institut(e) Institute of Ecological Chemistry (IOEC)
PSP-Element(e) G-505100-001
Scopus ID 44949091527
Erfassungsdatum 2008-10-28