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Solvent-Dependent Changes in the Triazolinedione-Alkene Ene Reaction Mechanism

机译：三唑啉二酮-烯烃烯反应机理的溶剂依赖性变化

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摘要

The influence of the solvent oil the triazolinedione-alkene ene reaction mechanism has been investigated. Both inter- and intramolecular kinetic isotope effects with tetramethylethylenes and 2.2.2-(trideuterio)methyl-7-methyl-2.6-octadiene-[D-3]-1.1.1 provide for the first time, strong evidence for chanocs in the mechanism of the reaction oil going from non-protic to polar protic solvents. In non-protic polar or apolar solvents, an aziridinium imide that equilibrates to an insignificantt extent with an open intermediate (a dipolar or a polarized biradical) is formed irreversibly in the first, rate-determining step of the reaction, which is followed by fast hydrogen abstraction. On the contrary, in polar protic solvents, hydrogen abstraction is rate limiting. allowing the main dipolar intermediate to equilibrate with its open intermediate(s) as well as with the starting reagents.
机译：研究了溶剂油对三唑啉二酮-烯烃反应机理的影响。四甲基乙烯和2.2.2-（三甲苯）甲基-7-甲基-2.6-辛二烯-[D-3] -1.1.1的分子间和分子内动力学同位素效应首次为该机理提供了有力的证据从非质子到极性质子溶剂的反应油。在非质子性极性或非极性溶剂中，在反应的第一个速率确定步骤中不可逆转地形成与开放中间体（偶极或极化双自由基）微不足道程度平衡的叠氮化亚胺，然后快速进行反应氢提取。相反，在极性质子溶剂中，氢的提取是限速的。使主要偶极中间体与其开放的中间体以及起始试剂达到平衡。

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