2024-03-29T13:58:30Z
https://nagoya.repo.nii.ac.jp/oai
oai:nagoya.repo.nii.ac.jp:00030143
2023-01-16T04:23:15Z
320:321:322
Cycloaddition of Dialkylalumanyl Anion toward Unsaturated Hydrocarbons in (1+2) and (1+4) Modes
Sugita, Kengo
Nakano, Ryo
Yamashita, Makoto
open access
This is the peer reviewed version of the following article: [K. Sugita, R. Nakano, M. Yamashita, Chem. Eur. J. 2020 , 26 , 2174.], which has been published in final form at [https://doi.org/10.1002/chem.201905830]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
alumanyl anions
aluminum
cycloaddition
density functional calculations
low oxidation states
The reactivity of dialkylalumanyl anion (1) towards naphthalene, anthracene, diphenylacetylene, and (E)/(Z)‐stilbenes was investigated. The compound 1 reacts with naphthalene and anthracene through (1+4) cyclization, giving Al‐containing norbornadiene derivatives. In the reaction of 1 with diphenylacetylene and (E)/(Z)‐stilbenes, (1+2) cyclization proceeded to form Al‐C‐C three‐membered rings. Cyclization toward (E)‐ or (Z)‐stilbenes solely gave a trans ‐cycloadduct. DFT calculations revealed that the cycloaddition of 1 with (Z)‐stilbene proceeds via a single transition state with a carbanion character, which results in the selectivity towards the trans ‐cycloadduct.
ファイル公開:2021-02-17
Wiley
2020-02-17
eng
journal article
AM
http://hdl.handle.net/2237/00032329
https://nagoya.repo.nii.ac.jp/records/30143
https://doi.org/10.1002/chem.201905830
0947-6539
Chemistry–A European Journal
26
10
2174
2177
https://nagoya.repo.nii.ac.jp/record/30143/files/Text20191224.pdf
application/pdf
619.7 kB
2021-02-17