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Updated: Jan 19, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
A newly designed heterodiene and its application to construct six-membered heterocycles containing an N-O bond
Wenzhi Ji1, Chen-Long Li2, Hui Chen1
1Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084, China. liaoxuebin@mail.tsinghua.edu.cn.
Abstract:
A new type of zwitterionic nitrosoalkene generated in situ from dehydrohalogenation of α-halo-N-alkylhydroxamic acids was designed. [4+2] cycloadditions of this heterodiene to olefins provide a facile route to construct six-membered heterocycles containing an N-O bond and a new protocol for 1,2-syn carbohydroxylate alkenes with a hydroxyl and acetamide group. DFT calculations support a concerted cycloaddition pathway and the solvent HFIP can stabilize the transition state through H-bonding interaction.
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Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...