Formation of 2‐(Phenylsulfonyl)resorcinols (=2‐(Phenylsulfonyl)benzene‐1,3‐diols) from Symmetrically Substituted Maleic Anhydrides (=Furan‐2,5‐diones) |
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| Authors: | Khaled Abou‐Hadeed Hans‐Jürgen Hansen |
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| Institution: | 1. Organisch‐chemisches Institut der Universit?t Zürich, Winterthurerstr. 190, CH‐8057 Zürich, (phone: +41‐44‐6354231;2. fax: +41‐44‐6356833) |
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| Abstract: | Treatment of symmetrically substituted maleic anhydrides (=furan‐2,5‐diones) 6 with lithium (phenylsulfonyl)methanide, followed by methylation of the adduct with MeI/K2CO3 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). |
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| Keywords: | C‐Methylation Maleic anhydrides Furan‐2 5‐diones Resorcinols 2‐(phenylsulfonyl)‐ Benzene‐1 3‐diols 2‐(phenylsulfonyl)‐ |
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