02136nas a2200217   4500008004100000022001400041245019200055210006900247260010600316300001400422490000700436520118400443653003201627653003801659653001801697653001501715653002001730100002201750700001901772856012701791       2006                        eng d  a0040-402000aHaval-Argade contrathermodynamic rearrangement of alkylidenesuccinimides to alkylmaleimides via the corresponding isoimides: a general approach to alkyl and dialkyl substituted maleimides0 aHavalArgade contrathermodynamic rearrangement of alkylidenesucci  aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcAPR  a3557-35630 v623 a<p>A simple and efficient access to alkyl and dialkyl substituted maleimides has been demonstrated via the new contrathermodynamic rearrangement of (E)-alkylidenesuccinimides to alkylinaleimides. The (E)-alkylidenesuccinimides obtained from the Wittig-condensation of N-arylmaleimide with aliphatic aldehydes oil regioselective hydrolysis furnished the corresponding (E)-alkylidenesuccinanilic acids in 95-98% yields. The beta-alkylidenesuccinanilic acids oil treatment with cyanuric chloride in the presence of triethylamine gave the corresponding beta-alkylisomaleimides in 78-80% yields via the beta-alkylideneisosuccinimides with the exocyclic to endocyclic carbon-carbon double bond migration. The kinetically controlled products alkylisomaleimides in refluxing acetic acid furnished the thermodynamically controlled alkylinaleimides in 98% yield. The Wittig condensation of alkyl substituted isomaleimides/maleimides with aliphatic aldehydes gave the desired dialkyl substituted maleimides in high yields. A conversion of alpha-methylenesuccinanilic acids to alpha-methylisomaleimides has also been described, with 90% yield. (c) 2006 Elsevier Ltd. All rights reserved.</p>10aalkyl and dialkylmaleimides10acontrathermodynamic rearrangement10aisomaleimides10amaleimides10awittig coupling1 aHaval, Kishan, P.1 aArgade, N., P.  uhttps://library.ncl.res.in/content/haval-argade-contrathermodynamic-rearrangement-alkylidenesuccinimides-alkylmaleimides-0