A Practical Synthesis and X-ray Crystallographic Analysis of Dithymoquinone, a Photodimer of Thymoquinone

Lett Org Chem. 2012 Dec 1;9(10):762-766. doi: 10.2174/157017812803901890.

Abstract

An updated and practical approach to the synthesis of dithymoquinone via one-step photoirradiation of thymoquinone (2-methyl-5-isopropyl-1,4-benzoquinone) is described. Synthesis resulted in a 55% yield of one structural isomer (trans-anti derivative), as confirmed by HPLC, NMR spectroscopy and first ever single-crystal X-ray diffraction analyses.

Keywords: X-ray structure; dithymoquinone; photodimerization; thymoquinone.