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

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...

Full description

Saved in:
Bibliographic Details
Published inAsian 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
LanguageEnglish
Published WEINHEIM Wiley 01.08.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TROPONOIDS
trimethylenemethane
troponoid
oxidation
CHEMISTRY
[6+3] cycloaddition
rearrangement
Online AccessGet more information

Cover

More Information
Summary: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 through acid-catalysed rearrangement of the derived mono-oxide to give the bicyclo[4.3.1]undecane 21.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900334