19283-81-9Relevant academic research and scientific papers
ORTHO-METHYLATION OF PHENOLS WITH ETHYL(IODOMETHYL)ZINC
Lehnert, Erich K.,Sawyer, J. Scott,Macdonald, Timothy L.
, p. 5215 - 5218 (2007/10/02)
The regioselective ortho-methylation of phenols by in situ generated ethyl(iodomethyl)zinc via an internal alkylation process is described.
Boron Trichloride as a Selective Demethylating Agent for Hindered Ethers: a Synthesis of the Phytoalexins α- and β-Pyrufuran, a Synthesis of Tri-O-methylleprolomin and its Demethylation
Carvalho, Christopher F.,Russo, Albert V.,Sargent, Melvyn V.
, p. 777 - 792 (2007/10/02)
Boron trichloride has been found to be an efficient reagent for the selective cleavage of sterically hindered methoxy groups in methoxyarenes.The scope and utility of this reaction are explored with examples drawn from derivatives of benzene, naphtalene, 9,10-dihydrophenanthrene and dibenzofuran.The method is applied to the synthesis of the phytoalexins α- (56) and β-pyrofuran (58) (1,3,4-trimethoxydibenzofuran-2-ol and 1,2,4-trimethoxydibenzofuran-3-ol).A synthesis of tri-O-methylleprolomin (61), a derivative of the unusual lichen metabolite leprolomin (60), is described and its demethylation with boron trichloride is studied.
