Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov Street 8, 420088 Kazan, Tatarstan, Russia.
Laboratory of Plant Infectious Diseases, FRC Kazan Scientific Center of Russian Academy of Sciences, Lobachevskogo Street 2/31, 420111 Kazan, Tatarstan, Russia.
J Org Chem. 2020 Nov 6;85(21):13472-13480. doi: 10.1021/acs.joc.0c01502. Epub 2020 Oct 14.
The reaction rates for the nucleophilic aromatic substitution of 4,6-dichloro-5-nitrobenzofuroxan with eight aliphatic amines (characterized by very different basicities/nucleophilicities) and three anilines have been measured in both methanol and toluene. The obtained rates have been related to the basicity (p in water and in benzene) or nucleophilicity ( Mayr constants) of the tested amines. The whole of the obtained kinetic data has furnished useful information on the high nucleophilic reactivity of benzofuroxan derivatives, which has been related essentially to two factors: the high electron-drawing ability/power of the condensed furoxan ring and the low aromatic character of the benzofuroxan system.
4,6-二氯-5-硝基苯并呋咱与 8 种脂肪族胺（具有非常不同的碱性/亲核性）和 3 种苯胺的亲核芳香取代反应速率已在甲醇和甲苯中进行了测量。所得速率与碱性（水中的 p 和苯中的 ）或亲核性（Mayr 常数）有关。测试的胺。所得的全部动力学数据提供了有关苯并呋咱衍生物高亲核反应性的有用信息，这主要与两个因素有关：缩合呋咱环的高吸电子能力/功率和苯并呋咱体系的低芳香性。
