期刊
TETRAHEDRON
卷 57, 期 15, 页码 3165-3174出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00175-2
关键词
IMDA reaction; furfurylamine; citraconic anhydride; citraconamic acid; substituent effects
Regioselectivity in the intra-molecular Diels-Alder (IMDA) reaction of furfurylcitraconamic acids derived from N-benzylfurfurylamines and citraconic anhydride can be controlled by substituents located in the furan ring and by reaction conditions. Reactions conducted under kinetic conditions resulted in cycloaddition products having methyl and aminomethylene substituent in 1,3-relationship whereas under thermodynamic conditions, excepting in the case of the 3-methylsulfanyl group, the products rearranged to more stable cycloadducts in which the substituents are in 1,2-relationship. Product formation can be explained on the basis of frontier orbital interactions and steric considerations. (C) 2001 Elsevier Science Ltd. All rights reserved.
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