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Accessing Light-Sensitive Polycyclic Aromatics through an Alkynyl-Prins Cyclization

Speer, Daniel John
Abstract
Phenyl-substituted 6H-naphtho[2,1-c]chromenes have been synthesized from 2-(3-hydroxy-4-phenylbut-1-yn-1-yl)phenol and para-substituted benzaldehydes using a cascade of reactions in one pot. This cascade is mediated by BF3·OEt2 and involves an alkynyl-Prins cyclization, Friedel-Crafts alkylation, and aromatization through the elimination of water to create the final chromene product. This sequence provides up to 92% yield of white or off-white solids. These products express interesting photochromic activity when exposed to UV light at 254nm, and vaguely resemble the structures of known cannabinoids. The structure of one product was verified by X-ray crystallographic analysis, showing non-planar ring structures.
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2018-04-01
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Undergraduate Honors Theses
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Hinkle, Robert J.
Scheerer, Jonathan
Abelt, Christopher
Rasmussen, Anne
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Chemistry
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https://scholarworks.wm.edu/handle/internal/10628
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