Regioselective Synthesis of 6‐[Chloro(difluoro)methyl]salicylates by [3+3] Cyclocondensations of 1,3‐Bis(trimethylsilyloxy)buta‐1,3‐dienes with 1‐Chloro‐1,1‐difluoro‐4‐(trimethylsilyloxy)pent‐3‐en‐2‐one |
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| Authors: | Silke Erfle Sebastian Reimann Alina Bunescu Zharylkasyn A. Abilov Anke Spannenberg Peter Langer |
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| Affiliation: | 1. Institut für Chemie, Universit?t Rostock, Albert Einstein Strasse 3a, D‐18059 Rostock;2. Leibniz‐Institut für Katalyse an der Universit?t Rostock e.V., Albert Einstein Strasse 29a, D‐18059 Rostock;3. Al‐Farabi Kazakh National University, Al‐Farabi ave. 71, 050040 Almaty, Kazakhstan |
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| Abstract: | ![]()
The TiCl4‐mediated [3+3] cyclocondensation of various 1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes with 1‐chloro‐1,1‐difluoro‐4‐(trimethylsilyloxy)pent‐3‐en‐2‐one provides a regioselective access to novel 6‐(chlorodifluoromethyl)salicylates (=6‐(chlorodifluoromethyl)‐2‐hydroxybenzoates) with very good regioselectivity. For selected products, it was demonstrated that the CF2Cl group can be transformed to CF2H and CF2(Allyl) by free‐radical reactions. |
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| Keywords: | Salicylates, 6‐[chloro(difluoro)methyl]‐ [3+3] Cyclocondensation Buta‐1,3‐dienes, 1,3‐bis(trimethylsilyloxy)‐ Pent‐3‐en‐2‐one, 1‐chloro‐1,1‐difluoro‐ |
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