The Synthesis, Structural Characterisation and Chemical Manipulation of the [6+3] Cycloadduct Derived from α-Tropolone O-Methyl Ether and Trimethylenemethane

• Published in: Asian journal of organic chemistry Vol. 8; no. 8; pp. 1458 - 1467
• Main Authors: Crisp, Antony L., Noble, Benjamin, Schwartz, Brett D., Willis, Anthony C., Coote, Michelle L., Banwell, Martin G.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.08.2019
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; TROPONOIDS; trimethylenemethane; troponoid; oxidation; CHEMISTRY; [6+3] cycloaddition; rearrangement
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.201900334

The title bicyclic system 3, the adduct arising from the formal [6+3] cycloaddition of alpha-tropolone O-methyl ether (1) and trimethylenemethane (2), has been prepared and subject to single-crystal X-ray analysis. The chemical manipulation of adduct 3 in a range of ways is reported, including throu...