Formation of 2‐(Phenylsulfonyl)resorcinols (=2‐(Phenylsulfonyl)benzene‐1,3‐diols) from Symmetrically Substituted Maleic Anhydrides (=Furan‐2,5‐diones) | Zendy

AbouHadeed Khaled | Zendy; Hansen HansJürgen | Zendy

Premium

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 ).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research