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2,5‐diphenyl‐3‐morpholinofuran and its 2‐hydro, 2‐bromo and 2‐hydroxymorpholinofurylium salts
Author(s) -
Lutz R. E.,
Hankins W. M.,
Hankins M. G.,
Welstead W. J.,
Dickerson C. L.
Publication year - 1970
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570070315
Subject(s) - chemistry , phenylmagnesium bromide , bromine , bromide , hydrogen bromide , medicinal chemistry , trifluoroacetic acid , morpholino , nmr spectra database , organic chemistry , spectral line , reagent , biochemistry , physics , astronomy , zebrafish , gene
2,5‐Diphenyl‐3‐morpholinofuran ( 1 ) reacts with bromine and trifluoroacetic acid, giving respectively 2‐bromo and 2‐hydro furylium salts ( 2,3 ). The 2‐hydroxy furylium bromide ( 4 ) was obtained by reaction of cis ‐morpholino‐1,2‐dibenzoylethylene ( 5 ) with hydrogen bromide. The nmr spectra of these salts show differences between the two morpholino dimethylene moieties of each caused by restricted rotation at the 3‐immonium group. Chemical relationships studied include reductions to the morpholinofuran, conversions to 3‐furanones, and the slow reaction of morpholinodibenzoylethylene with phenylmagnesium bromide to give cis ‐dibenzoylstyrene (13).