Unusual chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage

Shigehisa Tanji; Takanori Shibata; Itaru Sato; Kenso Soai

doi:10.1039/b009474i

Unusual chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage

Shigehisa Tanji, Takanori Shibata, Itaru Sato, Kenso Soai^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage was presented. It was shown that i-Pr₂Zn do not add to the aldehyde moiety but to the 2-position of the bipyridine to afford possessing a quaternary carbon atom in a yield of 69%. It was found that the i-Pr₂Zn does not add to the aldehyde but to the 2-position of the bipyridine ring by destroying the aromaticity of the pyridine ring.

Original language	English
Pages (from-to)	217-218
Number of pages	2
Journal	Journal of the Chemical Society. Perkin Transactions 1
Issue number	3
DOIs	https://doi.org/10.1039/b009474i
Publication status	Published - 2001 Feb 7
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1039/b009474i

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Unusual chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage. / Tanji, Shigehisa; Shibata, Takanori; Sato, Itaru et al.
In: Journal of the Chemical Society. Perkin Transactions 1, No. 3, 07.02.2001, p. 217-218.

Research output: Contribution to journal › Article › peer-review

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abstract = "The chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage was presented. It was shown that i-Pr2Zn do not add to the aldehyde moiety but to the 2-position of the bipyridine to afford possessing a quaternary carbon atom in a yield of 69%. It was found that the i-Pr2Zn does not add to the aldehyde but to the 2-position of the bipyridine ring by destroying the aromaticity of the pyridine ring.",

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AU - Shibata, Takanori

AU - Sato, Itaru

AU - Soai, Kenso

PY - 2001/2/7

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N2 - The chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage was presented. It was shown that i-Pr2Zn do not add to the aldehyde moiety but to the 2-position of the bipyridine to afford possessing a quaternary carbon atom in a yield of 69%. It was found that the i-Pr2Zn does not add to the aldehyde but to the 2-position of the bipyridine ring by destroying the aromaticity of the pyridine ring.

AB - The chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage was presented. It was shown that i-Pr2Zn do not add to the aldehyde moiety but to the 2-position of the bipyridine to afford possessing a quaternary carbon atom in a yield of 69%. It was found that the i-Pr2Zn does not add to the aldehyde but to the 2-position of the bipyridine ring by destroying the aromaticity of the pyridine ring.

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Unusual chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage

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