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Issue 18, 2000
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Reactions of diethyl azulene-1,3-dicarboxylate derivatives and 1-azaazulene derivatives with Grignard reagents, and alkyl- and aryllithium

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Abstract

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 ≫ 4 > 6, whereas reaction of 2-methoxy-1-azaazulene with a Grignard reagent gave 1-azaazulen-2(1H )-one.

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Article information


Submitted
17 Apr 2000
Accepted
17 Jul 2000
First published
23 Aug 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3063-3070
Article type
Paper

Reactions of diethyl azulene-1,3-dicarboxylate derivatives and 1-azaazulene derivatives with Grignard reagents, and alkyl- and aryllithium

T. Morita, N. Abe and K. Takase, J. Chem. Soc., Perkin Trans. 1, 2000, 3063
DOI: 10.1039/B003078N

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