On the regioselectivity of elimination reactions in terpene derivatives |
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| Affiliation: | 1. Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507 & FR3038, ENSICAEN, Normandie Université, Université de Caen Basse-Normandie, 6 Bd du Maréchal Juin, Caen 14050, France;2. Normandie Université, COBRA, UMR 6014 & FR 3038; Université de Rouen; INSA Rouen; CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France;3. CNRS, Institut de Pharmacologie et de Biologie Structurale, 205 Route de Narbonne, 31077 Toulouse, France;4. Université de Toulouse, UPS, IPBS, 205 Route de Narbonne, 31077 Toulouse, France;1. Saint-Petersburg State Technological Institute, Saint-Petersburg 190013, Russia;2. Ivanovo State University of Chemistry and Technology, Sheremetev ave. 7, 153000, Ivanovo, Russia;3. Science Institute, University of Iceland, Dunhaga 3, IS-107 Reykjavik, Iceland;1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka 565-0871, Japan;2. Osaka R&D Laboratory, Daihachi Chemical Industry Co., Ltd., 3-5-7 Chodo, Higashiosaka, Osaka 577-0056, Japan;3. The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan |
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| Abstract: | Tertiary alcohols with prenyl or geranyl moities, bearing a second oxygen. function in the 3, 4 or 5 position were dehydrated under various conditions : the composition of the olefinic mixture obtained was accounted for, by an intramolecular base relay effect.Basic elimination of analogous dimethylsutfonium salts gave results that could be related to the inductive effect : a correlation between regioselectivity and the Taft constantσI of the second oxygen function was found, except for the very basic alkoxide groups where an alternative regioselective elimination took place. |
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