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The Effect of Lewis Acids on the Cycloaddition of 3,3,6‐Trimethylcyclohex‐5‐ene‐1,2,4‐trione: Hydrogen Transfer versus Cycloaddition with Cyclopentadiene
Author(s) -
Eddy Nicholas A.,
Richardson Jay J.,
Fenteany Gabriel
Publication year - 2013
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.201300706
Subject(s) - cycloaddition , cyclopentadiene , chemistry , lewis acids and bases , catalysis , hydrogen , medicinal chemistry , organic chemistry
Exposure of 3,3,6‐trimethylcyclohex‐5‐ene‐1,2,4‐trione to catalytic amounts of Lewis acids revealed two disparate reactions in the presence of cyclopentadiene. The expected cycloaddition was found to be reversible for the title compound, and transfer hydrogenation was the preferred pathway over long periods of time. Other tested substrates were able to undergo facile cycloaddition with considerable yields and without the parallel reduction.