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Formation of 2‐(Phenylsulfonyl)resorcinols (=2‐(Phenylsulfonyl)benzene‐1,3‐diols) from Symmetrically Substituted Maleic Anhydrides (=Furan‐2,5‐diones)
Author(s) -
AbouHadeed Khaled,
Hansen HansJürgen
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300225
Subject(s) - chemistry , furan , adduct , lithium (medication) , medicinal chemistry , maleic anhydride , acetone , benzene , sulfone , organic chemistry , medicine , copolymer , endocrinology , polymer
Treatment of symmetrically substituted maleic anhydrides (=furan‐2,5‐diones) 6 with lithium (phenylsulfonyl)methanide, followed by methylation of the adduct with MeI/K 2 CO 3 in acetone, give the corresponding 4,5‐disubstituted 2‐methyl‐2‐(phenylsulfonyl)cyclopent‐4‐ene‐1,3‐diones 8 ( Scheme 3 ). Reaction of the latter with lithium (phenylsulfonyl)methanide in THF (−78°) and then with 4 mol‐equiv. BuLi (−5° to r.t.) leads to 5,6‐disubstituted 4‐methyl‐2‐(phenylsulfonyl)benzene‐1,3‐diols 9 ( Scheme 4 ).