Application of dioxinone derivatives for synthesis of aromatic compounds

Abstract

This thesis describes synthetic organic chemistry of 2,2,6-Trimethyl-4H-1,3-dioxin-4-one derivatives for the synthesis of aromatic compounds including salicylates, gamma resorcylates, hydroquinones and anilines. Using a biomimetic approach dioxinone derivatives acted as masked poly-carbonyl derivatives which cyclized giving the aromatic molecules in a de novo manner.

The synthesis of the substrates was carried out by a variety of methods to introduce different functional groups prior to cyclization. Cross metathesis of a vinyl dioxinone gave access to a variety of substrates capable of cyclization to give salicylates, gamma resorcylates, hydroquinones and anilines. Use of aldol additions to keto-dioxinone compounds gave rise to substrates for formation of gamma resorcylates.

Furthermore, the different routes for the synthesis of the substrates are discussed in detail and with reference to unsuccessful strategies also attempted. This includes details of the synthesis of dioxinone derivatives that may be useful in other unexplored applications.

The introduction examines existing strategies for de novo aromatic synthesis, highlighting numerous different approaches and making direct comparisons between them where possible. Also reported is previous research into dioxinone compounds and applications in synthesis of aromatic molecules. Experimental material detailing the procedures carried out and data obtained are included at the end.