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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
2,2'-Spirobis[chromene] Derivatives Chemistry and Their Relation with the Multistate System of Anthocyanins
Artur J Moro1, A Jorge Parola1, Fernando Pina1
1LAQV-REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa , 2829-516 Caparica, Portugal.
Abstract:
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.
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