An Unusual Acid-Induced Retro Dieckmann Condensation Reaction

酸誘導逆狄克曼縮合反應

周大紓(Ta-Shue Chou) ； 曾淑惠(Shu-Huey Tseng) ； 陳宏銓(Hong-Chuan Chen)

《中央研究院化學研究所集刊》 43期 (1996/03) Pp. 109-116

https://doi.org/10.6522/BICAS.1996.43.10

摘要

在試圖製備2-甲氧羰基-1-碸環戊-3-酮（1）時，我們觀察到了幾個非常有趣的反應。2-（甲氧羰甲磺基）丙酸酯（10）在鹼性條件下很意外的不進行狄克曼縮合反應，卻很快的進行脫去反應。而3,3-伸乙二氧-1-碸環戊基-2-甲酸酯在酸性條件下進行了極不尋常的酸誘導逆狄克曼縮合反應。

並列摘要

During the attempts to prepare 2-methoxycarbonyl-3-sulfolanone 1, several interesting reactions were observed. 2-[(Methoxycarbonyl) methanesulfonyl] propanoate 10 was found to undergo facile elimination instead of Dieckmann condensation under basic conditions. 3, 3-Ethylenedioxysulfolane-2-carboxylate 15 was found to undergo an unusual acid-induced retro Dieckmann condensation reaction.