Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

2,2′-Spirobis[chromene] Derivatives Chemistry and Their Relation with the Multistate System of Anthocyanins

2,2′-Spirobis[chromene] Derivatives Chemistry and Their Relation with the Multistate System of Anthocyanins
Artur J. Moro, A. Jorge Parola, Liliana Cseh, Fernando Pina, Ana-Maria Pana, Valentin Badea, Sergiu Shova, Iulia Pausescu
The chemistry of 2,2′-spirobis[chromene] derivatives is intimately related to the one of anthocyanins and similar compounds. The 2,2′-spirobis[chromene] species plays a central role in the network of chemical reactions connecting two different flavylium-based multistate systems. In the present work, a new asymmetric 2,2′-spirobis[chromene] intermediate possessing a constrained propylenic bridge between carbons 3 and 3′ was isolated and its role as a pivot in the anthocyanins-type multistate of chemical reactions was investigated by the conjugation of absorption spectroscopy, stopped-flow, NMR, and X-ray crystallography. It was confirmed that the propylenic bridge is essential to stabilize the spirobis[chromene] species. Furthermore, under acidic conditions, two cis–trans styrylflavylium isomers were identified, which could be interconverted directly into one another with light. This is the first report of styrylflavylium cations with photoisomerization on the styryl moiety.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00634

DOI: 10.1021/acs.joc.7b00634

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