engleski

Microwave reactions of 2, 5-bis-trifluoromethyl-1, 3, 4-oxadiazole with norbornenes

The reactions of 2, 5-bis-trifluoromethyl-1, 3, 4- oxadiazole 2 with norbornenes [1] under microwave conditions were investigated. MW reactions enabled the reaction times and temperatures to be significantly reduced, as compared to classical thermal reactions. Furthermore, unprecedented stereochemical outcome of the reaction with 7- oxanorbornenes 1 was found, where linear product 4 was isolated, alongside usual bent-shaped cycloadduct 3 [2]. The reaction mechanism was investigated computationally by density functional methods (B3LYP/6-31G*), and stereochemical results explained by stereoelectronic reasons [3]. [1] R. N. Warrener, D. Margetić, R. A. Russell, Synlett (1998) 585. [2] R. N. Warrener, Eur. J. Org. Chem. (2000) 3363. [3] D. Margetić, R. N. Warrener, Croat. Chem. Acta. 76 (2003) 357.

microwave reactions; cycloadditions; quantum chemical calculations

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