Sreenivas, Kukkamudi and Khan, Faiz Ahmed
(2019)
FeCl3 catalyzed 1,6-conjugate addition of phenol C-nucleophiles: Facile synthesis of diarylmethanes.
Tetrahedron.
ISSN 0040-4020
(In Press)
Full text not available from this repository.
(
Request a copy)
Abstract
An efficient synthesis of diarylmethane derivatives from phenol and a p-quinone methide surrogate cyclohexadienone derivative has been described. This 1,6-conjugate addition reaction is catalyzed by earth abundant FeCl3 and it proceeds via a consecutive Michael type addition followed by aromatization. Various proportions of phenol and cyclohexadienone produced exclusively mono, bis and tris addition products. Interestingly, di-tert-butylphenol gave addition product with concomitant loss of one of the tertiary butyl groups of the phenol moiety via retro-Friedel-Crafts reaction. This strategy demonstrates a straightforward access to wide range of diarylmethane derivatives possessing biologically significant ortho-methoxyphenol moiety under mild reaction conditions.
Actions (login required)
 |
View Item |