N-氟烷基三唑的Aza-Wolff重排反应生成烯酮胺†

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI:10.1039/d3qo00618b

Anna Kubíčková , Athanasios Markos , Svatava Voltrová , Anežka Marková , Josef Filgas , Blanka Klepetářová , Petr Slavíček , Petr Beier

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引用次数: 0

摘要

N-氟烷基化的1,2,3-三唑经过微波加热辅助开环、氮分子消除和伴随的基团重排，形成可分离的N-氟烷基烯酮胺。这种无试剂工艺的特点是范围广、效率高，为制备未开发的N-氟烷基化合物提供了一条新途径。反应机理通过机理和计算研究相结合的方法进行了研究。烯酮胺与炔烃或烯烃的[2+2]环加成分别得到新的环丁烯亚胺和环丁亚胺。将氧、硫和氮亲核试剂添加到烯酮胺中，得到新的N-氟烷基酰亚胺、硫代酰亚胺和脒。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Aza-Wolff rearrangement of N-fluoroalkyl triazoles to ketenimines†

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Aza-Wolff rearrangement of N-fluoroalkyl triazoles to ketenimines†

N-Fluoroalkylated 1,2,3-triazoles underwent a microwave-heating-assisted ring opening, nitrogen molecule elimination and concomitant group rearrangement to form isolable N-fluoroalkylketenimines. This reagent-free process is characterized by a wide scope and high efficiency and provides a new route to unexplored N-fluoroalkyl compounds. The reaction mechanism was investigated by a combination of mechanistic and computational studies. [2 + 2] cycloaddition of ketenimines with alkynes or alkenes afforded novel cyclobutenimines and cyclobutanimines, respectively. Addition of oxygen-, sulfur- and nitrogen nucleophiles to ketenimines gave new N-fluoroalkyl imidates, thioimidates and amidines.

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来源期刊

Organic chemistry frontiers : an international journal of organic chemistry

CiteScore

7.80

自引率

0.00%

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