Synthesis of polysubstituted 3-thiofurans by regiospecific mono- ipso-substitution and ortho-metallation from 3,4-dibromofuran

The synthetic potential of 3,4-dibromofuran has been assessed by its conversion into 3,4-disubstituted furans via mono- S- ipso-substitution. The ability of 3-methylthio and 3-phenylthio substituents for directing the metallation at position α-relative to the substituent has allowed the regiospecifi...

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Bibliographic Details
Published in:Tetrahedron 1996-03, Vol.52 (11), p.4065-4078
Main Authors: Alvarez-Ibarra, Carlos, Quiroga, Maria L., Toledano, Emilio
Format: Article
Language:English
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Summary:The synthetic potential of 3,4-dibromofuran has been assessed by its conversion into 3,4-disubstituted furans via mono- S- ipso-substitution. The ability of 3-methylthio and 3-phenylthio substituents for directing the metallation at position α-relative to the substituent has allowed the regiospecific alkylation. It provides a straightforward approach to several 3-monothiosubstituted furans which are receiving increasing interest as odour and flavour chemicals. Polysubstituted 3-thiofurans which are receiving a great interest as flavour and odour chemicals have been obtained by mono- ipso-susbtitution and ortho-metallation from 3,4-dibromofuran (E 1: H, Br, Me, SMe; E 2: Me, Et, SMe, SPh, SCOMe, SCOPh; E 3: Me, SPh).
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(96)00069-5