Date Thesis Awarded

4-2018

Document Type

Honors Thesis

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Robert J. Hinkle

Committee Members

Jonathan Scheerer

Christopher Abelt

Anne Rasmussen

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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This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

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