Journal
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Volume -, Issue 18, Pages 3063-3070Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b003078n
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Reactions of diethyl azulene-1,3-dicarboxylate (1) and diethyl 2-chloroazulene-1,3-dicarboxylate (11) with Grignard reagents, followed by dehydration with tetrachloro-1,2-benzoquinone, gave 2-, 4,- and 6-substituted addition-oxidation products. Grignards reagents have a tendency to react with 1 at the positions in the order of 2>4>6, while steric hindrance has a greater influence at the positions in order of 2>4>6. Reactions of 1 and 11 with phenyllithium and methyllithium gave similar results. On the other hand, on the reaction of diethyl 2-methoxyazulene-1,3-dicarboxylate (15), Grignard reagents attacked preferentially at the methoxy group, and 2-substituted products were obtained. Use of excess molar equivalents of Grignard reagents led to diaryl-substituted products. Reaction of 2-chloro-1-azaazulenes with Grignard reagents also gave similar addition-oxidation products, and reacted at the positions in the order 8 much greater than 4>6, whereas reaction of 2-methoxy-1-azaazulene with a Grignard reagent gave 1-azaazulen-2(1H)-one.
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