111787-91-8Relevant articles and documents
Photochemical Alkene Isomerization for the Synthesis of Polysubstituted Furans and Pyrroles under Neutral Conditions
Walker, Johannes C. L.,Werrel, Simon,Donohoe, Timothy J.
supporting information, p. 13114 - 13118 (2019/10/22)
A photochemical approach to polysubstituted heterocycles using UV-induced alkene isomerization is described. The method allows for the synthesis of disubstituted furans and pyrroles under mild and neutral conditions and also provides access to a class of trisubstituted furans pertinent to natural-product synthesis. The method has broad functional-group tolerance and many richly decorated heterocycles have been prepared incorporating functional groups that are unstable under Br?nsted and Lewis acidic conditions.
Halomethyl derivatives of 2-phenylfurans in the Arbuzov and Michaelis-Becker reactions
Pevzner,Ignat'ev,Ionin
, p. 917 - 921 (2007/10/03)
The α-phenyl substituent in 3-(chloromethyl)furan, nonconjugated with the reaction center, does not hinder the nucleophilic attack of phosphite anion under conditions of the Michaelis-Becker reaction, while in the isomer with a conjugated phenyl substituent the halogen atom is attacked under the same conditions. Reaction of the latter with trimethyl phosphite yields the corresponding phosphonate. Phosphorylation of 5-(bromomethyl)-2-phenylfuran derivatives containing acceptor substituents in the β-position of the furan ring with trimethyl phosphite in the presence of amyl alcohol as proton donor involves no attack of the phosphite on the halogen atom and the products of the classic Arbuzov reaction are formed.