open access

https://hdl.handle.net/2115/95894

Synthesis and Conformational Analysis of α,β-Dichlorocarbonyl Compounds

英語

Conformational analysis

2024-09-02

Wiley-Blackwell

European journal of organic chemistry

27(33)

e202400489

α,β-Dichlorocarbonyl compounds were synthesized by facile dichlorination of α,β-unsaturated amides with TCIA-PPh3 and the resultant amides were converted to ketones. Conformational analyses of the products were performed to confirm our previous hypothesis regarding vicinal dichlorinated carbonyl compounds. The compounds exhibited 1 H NMR signals with large coupling constants (7-11 Hz) for the 1,2-anti-configuration and small coupling constants (3-4 Hz) for the 1,2-syn-configuration. The syn-pentane interaction enabled rational conformational analysis of the α,β-dichlorinated carbonyl compounds, although some interesting exceptions were observed. Consideration of these conformations is helpful in assigning relative configurations of α,β-dihalogenated carbonyl compounds in general.

学術雑誌論文

Accepted Manuscript

This is the peer reviewed version of the following article: Shunta Kobayashi, Nurcahyo Iman Prakoso, Xin Zheng, Shin-ichiro Noro, Masaru Hashimoto, Tatsuya Morozumi, Taiki Umezawa. Synthesis and Conformational Analysis of α,β-Dichlorocarbonyl Compounds. European journal of organic chemistry. 2024, Volume27, Issue33, e202400489, which has been published in final form at https://doi.org/10.1002/ejoc.202400489. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

1434-193X