118041-91-1Relevant academic research and scientific papers
Synthesis of p-Chlorophenols (and -naphthols) from the Thermal Rearrangement of 4-Chlorocyclobutenones
Xu, Simon L.,Moore, Harold W.
, p. 326 - 338 (2007/10/02)
A systematic study of the reaction of 4-hydroxycyclobutenones with thionyl chloride is reported.A useful model evolves from this study which allows the prediction of the site of chlorination for unsymmetrical examples.The chlorination is envisaged to invo
Rearrangement of 4-Alkynylcyclobutenones. A New Synthesis of 1,4-Benzoquinones
Foland, Lafayette D.,Karlsson, J. Olle,Perri, Steven T.,Schwabe, Rudolf,Xu, Simon L.,et al.
, p. 975 - 989 (2007/10/02)
A new convergent synthesis of 1,4-benzoquinones from 4-alkynyl-4-alkoxy(or hydroxy or trimethylsilyloxy)cyclobutenones is described.The required cyclobutenones are prepared from squaric acid and converted to the quinones upon mild thermolysis.The reaction proceeds via electrocyclic ring opening of the required cyclobutenones to (2-alkynylethenyl)ketenes, which then ring close to unique diradical intermediates.These then give the quinone products.The scope and mechanism of this unusual rearrangement are discussed.
