Gold‐Catalyzed Rearrangements: Reaction Pathways Using 1‐Alkenyl‐2‐alkynylcyclopropane Substrates | Zendy

Barluenga José | Zendy; Tudela Eva | Zendy; Vicente Rubén | Zendy; Ballesteros Alfredo | Zendy; Tomás Miguel | Zendy

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Gold‐Catalyzed Rearrangements: Reaction Pathways Using 1‐Alkenyl‐2‐alkynylcyclopropane Substrates

Author(s) -

Barluenga José,

Tudela Eva,

Vicente Rubén,

Ballesteros Alfredo,

Tomás Miguel

Publication year - 2011

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201007795

Subject(s) - octane , catalysis , chemistry , bicyclic molecule , reactivity (psychology) , cleavage (geology) , ring (chemistry) , bond cleavage , stereochemistry , medicinal chemistry , organic chemistry , materials science , medicine , alternative medicine , pathology , fracture (geology) , composite material

New reactivity patterns : Gold(I) catalyzes the conversion of cyclopentenes ( 1 / 1′ ) into cyclohexadienes ( 2 / 3 ). This profound skeleton rearrangement comprises ring expansion and a [1,2]‐alkynyl shift, and is thought to be initiated by the cleavage of the bridging CC bond. The proposed allyl–gold cation intermediate is trapped with alcohols to provide bicyclo[3.2.1]octadiene and tricyclo[3.2.1.0 2,7 ]octane derivatives.

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