6-氟环己-1,2,4-三烯中间体的生成[通过四氢- diels - alder反应]和反应性。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-01 DOI:10.1021/acs.orglett.5c03636

Paul V Kevorkian,Thomas R Hoye

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引用次数: 0

摘要

我们报道了2,6-二氟苯基取代基在十四氢- diels - alder （TDDA）反应中的作用。氟的使用是由DFT计算指导的。底物中酸酐连接剂加速TDDA环异构化也是关键。外杂环、烯醇和烯烃中的亲核碳捕获张力环烯烯中间体，导致不寻常的反应性（例如，通过重排到碳烯中间体而合理化）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Generation [via Tetradehydro-Diels-Alder Reactions] and Reactivity of 6-Fluorocyclohexa-1,2,4-triene Intermediates.

We report the engagement of the 2,6-difluorophenyl substituent in tetradehydro-Diels-Alder (TDDA) reactions. The use of fluorine was guided by DFT computations. Acceleration of TDDA cycloisomerization by an anhydride linker in the substrates was also key. Trapping of the strained cyclic allene intermediate by nucleophilic carbons in external heterocycles, an enol, and alkenes led to unusual reactivities (e.g., one rationalized by rearrangement to a carbene intermediate).

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.