TY - JOUR
T1 - Thermally induced [2+2] cycloadditions of (benzyloxymethylene)cyclopropane with alkylidenemalononitriles
AU - Nakamura, Itaru
AU - Nagata, Ryoko
AU - Nemoto, Tetsuya
AU - Terada, Masahiro
AU - Yamamoto, Yoshinori
AU - Späth, Thomas
AU - De Meijere, Armin
PY - 2007
Y1 - 2007
N2 - The reaction of (benzyloxymethylene)cyclopropane (1a) with alkylidenemalononitriles 2 at ambient pressure afforded the corresponding cyclobutane derivatives 3 in good-to-high yields. For example, the reaction of 1a with benzylidenemalononitrile (2a), (2-naphthylmethylene)malononitrile (2e), and tert-butylmethylenemalononitrile (2f) in acetonitrile at 80°C gave the corresponding cyclobutanes 3a, 3e, and 3f in 96, 96, and 91% yield, respectively. Control experiments proved that the reaction proceeds via well-stabilized zwitter-ionic intermediate 6.
AB - The reaction of (benzyloxymethylene)cyclopropane (1a) with alkylidenemalononitriles 2 at ambient pressure afforded the corresponding cyclobutane derivatives 3 in good-to-high yields. For example, the reaction of 1a with benzylidenemalononitrile (2a), (2-naphthylmethylene)malononitrile (2e), and tert-butylmethylenemalononitrile (2f) in acetonitrile at 80°C gave the corresponding cyclobutanes 3a, 3e, and 3f in 96, 96, and 91% yield, respectively. Control experiments proved that the reaction proceeds via well-stabilized zwitter-ionic intermediate 6.
KW - Cycloaddition
KW - Cyclobutanes
KW - Cyclopropanes
KW - Enols
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U2 - 10.1002/ejoc.200700531
DO - 10.1002/ejoc.200700531
M3 - Article
AN - SCOPUS:34748866709
SN - 0075-4617
SP - 4479
EP - 4482
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
IS - 27
ER -