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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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使用受控的Friedel-Crafts反应合成新大麻素

Alexandra M Millimaci1, Richard V Trilles1, James H McNeely1

  • 1Department of Chemistry, Boston University, Boston, Massachusetts 02215, United States.

The Journal of organic chemistry
|September 1, 2023
PubMed
概括

介绍了一种新的一步合成8,9-二二 (H2CBD) 和新可纳比诺基的方法. 这种方法利用受控的Friedel-Crafts反应,通过实验和计算研究提供了对区域选择性的见解.

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Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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