کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1314204 | 975952 | 2010 | 6 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Ab initio study of the mechanism of the formation of p-rosolic acid from trifluoromethoxybenzene under HF/Lewis acid conditions
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی معدنی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
The mechanism of the formation of p-rosolic acid from trifluoromethoxybenzene under HF/Lewis acid conditions was studied using ab initio methods. A series of cationic intermediates is initiated by the expulsion of a fluorine atom of trifluoromethoxybenzene with anomeric assistance of the trifluoromethoxy oxygen. The resulting difluorocarbonium ion is attacked by a second trifluoromethoxybenzene to generate the first carbon-carbon bond on what will be the central carbon of p-rosolic acid. Elimination of phenol results in the formation of cationic intermediate 4 which is susceptible to carbon-alkylation by the same phenol to form the second carbon-carbon bond. Attack on subsequent difluorocarbonium ions by trifluoromethoxybenzene strips trifluoromethyl groups from the downstream intermediates, eventually leading to p-rosolic acid, and continues the generation of 4, each of which initiate a fresh mechanistic series toward another p-rosolic acid molecule.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Fluorine Chemistry - Volume 131, Issue 12, December 2010, Pages 1308-1313
Journal: Journal of Fluorine Chemistry - Volume 131, Issue 12, December 2010, Pages 1308-1313
نویسندگان
Randolph K. Belter, Cheri A. McFerrin,