以一鍋反應使芳基磺醯氯與具有活性之烯烴在水中進行共軛加成

Conjugate Addition of Arenesulfonyl Chloride with Activated Olefins by One-pot Reaction in Water

陳彥洲(YEN-CHOU CHEN)

指導教授 ： 蔡福裕

國立臺北科技大學/工程學院/有機高分子研究所/碩士(2014年)

https://doi.org/10.6841/NTUT.2014.00083

摘要

我們利用芳基磺醯氯與各類烯烴以一鍋反應的方式進行共軛加成，首先芳烴磺醯氯先與亞硫酸鈉以及碳酸氫鈉反應形成亞磺酸鈉鹽後，在相同反應條件下與烯烴反應，進而得到共軛加成的產物。此反應之反應條件為在空氣下攝氏80度水中反應，其反應性佳。一般來說，這類亞磺酸鹽必須以乙醇再結晶純化才能取得，因此，此實驗最大的優點在於不需要純化亞磺酸鹽即可進行一鍋反應的共軛加成，減少了許多溶劑上的浪費。

關鍵字

磺醯氯 ； 共軛加成 ； 一鍋反應

並列摘要

In this study, we first use a one-pot reaction system of conjugate addition, arenesulfonyl chlorides are reacted with sodium sulfite and sodium bicarbonate and produce the arenesulfinic acid sodium salts. Second, the arenesulfinic acid sodium salts are reacted with activated olefins. Finally we acquire the conjugate addition products. This one-pot reaction is conducted in air at 80℃, providing the corresponding products in medium to good yields. Conventionally, arenesulfinic acid sodium salts need to be purified by recrystallization in ethanol. There is an advantage in our work that the reaction does not need to purify arenesulfinic acid sodium salts, and arenesulfinic acid sodium salts can be reacted with activated olefins.

並列關鍵字

arenesulfonyl chloride ； one-pot ； conjugate addition

參考文獻

[1] Paul T. Anastas, John C. Warner, Green Chemistry Theory & Practice, Oxford University Press, 1998.

[3] Fink, Johannes, High Performance Polymers. Norwich: William Andrew, 2008.

[4] C. Liao; Liu, F.; Kannan, K. Environ. Sci. Technol. 2012, 46, 6515.

[6] Pocket Medicine, The Massachusetts General Hospital Handbook of Internal Medicine, Sabatine, 3rd Edition.

[8] Rogers, RS.; Seehafer, JR.; Perry, HO. J. Am. Acad. Dermatol. 1982, 6, 215.