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3 results on '"methylenecyclobutanes"'

1. Synthesis of (2-Arylethylidene)cyclobutanes by Palladium-Catalyzed Reactions of Aryl Halides with Homoallyl Alcohols Bearing a Trimethylene Group at the Allylic Position

Author

Koichiro Oshima, Hideki Yorimitsu, and Masayuki Iwasaki

Subjects
inorganic chemicals, chemistry.chemical_classification, Cyclobutanes, Allylic rearrangement, Double bond, organic chemicals, Aryl, Organic Chemistry, food and beverages, chemistry.chemical_element, Halide, methylenecyclobutanes, palladium, Medicinal chemistry, Catalysis, cleavage reactions, chemistry.chemical_compound, chemistry, Group (periodic table), Organic chemistry, homoallyl alcohols, allylation, Palladium
Abstract

Treatment of aryl bromides with homoallyl alcohols bearing a trimethylene group at the allylic position in the presence of cesium carbonate under palladium catalysis affords (2-aryl­ethylidene)cyclobutanes selectively. The selective formation of the alkylidenecyclobutane skeleton results from regiospecific retro-­allylation of the homoallyl alcohols, which accompanies the transposition of the double bonds.

Published
2009

2. Synthesis of (2-Arylethylidene)cyclobutanes by Palladium-Catalyzed Reactions of Aryl Halides with Homoallyl Alcohols Bearing a Trimethylene Group at the Allylic Position

Author

00372566, 00111922, Iwasaki, Masayuki, Yorimitsu, Hideki, Oshima, Koichiro, 00372566, 00111922, Iwasaki, Masayuki, Yorimitsu, Hideki, and Oshima, Koichiro

Abstract

Treatment of aryl bromides with homoallyl alcohols bearing a trimethylene group at the allylic position in the presence of cesium carbonate under palladium catalysis affords (2-aryl­ethylidene)cyclobutanes selectively. The selective formation of the alkylidenecyclobutane skeleton results from regiospecific retro-­allylation of the homoallyl alcohols, which accompanies the transposition of the double bonds.

Published
2009

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