Boron trichloride as a selective demethylating agent for hindered ethers

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

Australian Journal of Chemistry ◽

10.1071/ch9850777 ◽

1985 ◽

Vol 38 (5) ◽

pp. 777 ◽

Cited By ~ 16

Author(s):

CF Carvalho ◽

AV Russo ◽

MV Sargent

Keyword(s):

Boron Trichloride ◽

Demethylating Agent ◽

Methoxy Groups ◽

Sterically Hindered ◽

Derivatives Of ◽

Lichen Metabolite ◽

Efficient Reagent

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, naphthalene, 9,10- dihydrophenanthrene and dibenzofuran. The method is applied to the synthesis of the phytoalexins α-(56) and β- pyrufuran (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.

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ChemInform Abstract: BORON TRICHLORIDE AS A SELECTIVE DEMETHYLATING AGENT FOR HINDERED ETHERS

Chemischer Informationsdienst ◽

10.1002/chin.198427121 ◽

1984 ◽

Vol 15 (27) ◽

Author(s):

C. F. CARVALHO ◽

M. V. SARGENT

Keyword(s):

Boron Trichloride ◽

Demethylating Agent

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ChemInform Abstract: 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.

Chemischer Informationsdienst ◽

10.1002/chin.198541124 ◽

1985 ◽

Vol 16 (41) ◽

Author(s):

C. F. CARVALHO ◽

A. V. RUSSO ◽

M. V. SARGENT

Keyword(s):

Boron Trichloride ◽

Demethylating Agent

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Boron trichloride as a selective demethylating agent

Tetrahedron Letters ◽

10.1016/s0040-4039(00)76028-x ◽

1966 ◽

Vol 7 (35) ◽

pp. 4153-4159 ◽

Cited By ~ 81

Author(s):

F.M. Dean ◽

J. Goodchild ◽

L.E. Houghton ◽

J.A. Martin ◽

R.B. Morton ◽

...

Keyword(s):

Boron Trichloride ◽

Demethylating Agent

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Nitrones and Oxaziridines. XXXVI. Synthesis of Cyclic Thiohydroxamic Acids

Australian Journal of Chemistry ◽

10.1071/ch9880037 ◽

1988 ◽

Vol 41 (1) ◽

pp. 37 ◽

Cited By ~ 2

Author(s):

DS Black ◽

KL Ooi

Keyword(s):

Hydroxamic Acids ◽

Demethylating Agent ◽

Ethyl Xanthate ◽

Cyclic Hydroxamic Acids ◽

Trimethylsilyl Iodide ◽

Potassium Ethyl Xanthate

2-Cyano-1-pyrroline 1-oxides (1) could not be converted directly into the related cyclic thiohydroxamic acids (8). Potassium ethyl xanthate transformed nitrones (1) into the imidates (2). The cyclic hydroxamic acids (4) can be converted into the thiohydroxamic acids (8) via the methoxypyrrolidinones (5) and the methoxypyrrolidine thiones (6), making use of sodium p- tolylmercaptide as the demethylating agent. Reaction of methoxy thiones (6) with trimethylsilyl iodide led to the formation of the 2-methylthio-1-pyrroline 1-oxides (7).

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