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Oxidative Isomerization of Vinylidenecyclopropanes to Dimethylenecyclopropanes and Brønsted Acid‐Catalyzed Further Transformation
Author(s) -
Lu BeiLi,
Shi Min
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001484
Subject(s) - isomerization , chemistry , brønsted–lowry acid–base theory , catalysis , oxidative phosphorylation , indene , scope (computer science) , transformation (genetics) , oxide , photochemistry , organic chemistry , medicinal chemistry , combinatorial chemistry , biochemistry , gene , computer science , programming language
Oxidative isomerization of vinylidenecyclopropanes 1 produces dimethylenecyclopropane aldehydes 2 in moderate to good yields using tetrapropylammonium perruthenate (TPAP)/4‐methylmorpholine N ‐oxide (NMO) as a catalytic system and the obtained dimethylenecyclopropanes 3 can be transformed to indene derivatives smoothly in the presence of Brønsted acid (HOTf). The scope and limitations as well as the plausible mechanisms have been discussed.