DOI: 10.1246/bcsj.52.2036. Chemistry of Dienyl Anions. I. Crystalline Dienyl Anions by Direct Reaction of Conjugated and Non-conjugated Dienes with Alkali Metals in the Presence of Et3N

Chemistry of Dienyl Anions. I. Crystalline Dienyl Anions by Direct Reaction of Conjugated and Non-conjugated Dienes with Alkali Metals in the Presence of Et3N

10.1246/bcsj.52.2036

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Series of acyclic and cyclic dienyl anions were prepared from both conjugated and non-conjugated dienes by direct metalation with alkali metals (Li, Na, K, Rb, and Cs) in tetrahydrofuran in the presence of triethylamine or N,N,N′,N′-tetramethylethylenediamine. Eight different dienyl anions of open chain or cyclic structures were isolated as crystals. All the acyclic potassium dienides of pentadienes, 2-methylpentadienes, 3-methylpentadienes, hexadienes and 2,4-dimethylpentadienes gave the corresponding 1,3-dienes upon hydrolysis, while the potassium cyclic dienide of cycloheptadienes and cyclooctadienes gave 1,4-dienes exclusively. The result of methylation of dienyl anions with methyl iodide agreed with that of hydrolysis. The reaction path for formation of these dienyl anions was studied based on the carbon skeleton and the molar ratio of the reduced diene dimers produced together with the dienyl anions. Selective oxidative coupling of the dienyl anions occurred with CuX or CuX2 to give linear tetraenes in good yield.

Bibliography

Yasuda, H., Ohnuma, Y., Yamauchi, M., Tani, H., & Nakamura, A. (1979). Chemistry of Dienyl Anions. I. Crystalline Dienyl Anions by Direct Reaction of Conjugated and Non-conjugated Dienes with Alkali Metals in the Presence of Et3N. Bulletin of the Chemical Society of Japan, 52(7), 2036â2045.

Authors 5

Hajime Yasuda (first)
Yasuo Ohnuma (additional)
Michihide Yamauchi (additional)
Hisaya Tani (additional)
Akira Nakamura (additional)

References 48 Referenced 72

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Dates

Type	When
Created	19 years, 1 month ago (July 19, 2006, 7:15 p.m.)
Deposited	1 year, 7 months ago (Jan. 17, 2024, 8:18 a.m.)
Indexed	1 year, 7 months ago (Jan. 19, 2024, 5:57 a.m.)
Issued	46 years, 2 months ago (July 1, 1979)
Published	46 years, 2 months ago (July 1, 1979)
Published Online	19 years, 4 months ago (April 19, 2006)
Published Print	46 years, 2 months ago (July 1, 1979)

Funders 0

None

BibTeX

@article{Yasuda_1979, title={Chemistry of Dienyl Anions. I. Crystalline Dienyl Anions by Direct Reaction of Conjugated and Non-conjugated Dienes with Alkali Metals in the Presence of Et3N}, volume={52}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.52.2036}, DOI={10.1246/bcsj.52.2036}, number={7}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Yasuda, Hajime and Ohnuma, Yasuo and Yamauchi, Michihide and Tani, Hisaya and Nakamura, Akira}, year={1979}, month=jul, pages={2036–2045} }

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