A Study of the Conjugate Addition of Thionucleophiles to 2(5 H )‐Furanones | Zendy

Busqué Felix | Zendy; de March Pedro | Zendy; Figueredo Marta | Zendy; Font Josep | Zendy; González Lluïsa | Zendy

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A Study of the Conjugate Addition of Thionucleophiles to 2(5 H )‐Furanones

Author(s) -

Busqué Felix,

de March Pedro,

Figueredo Marta,

Font Josep,

González Lluïsa

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300693

Subject(s) - chemistry , conjugate , thio , electrophile , addition reaction , adduct , substrate (aquarium) , hydrolysis , thiol , medicinal chemistry , organic chemistry , stereochemistry , catalysis , mathematical analysis , oceanography , mathematics , geology

Several new 4‐thio‐4,5‐dihydro‐2(3 H )‐furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5 H )‐furanones. When 5‐methyl‐2(5 H )‐furanone was used as the electrophilic substrate, the reaction was diastereoselective affording exclusively the cis ‐α,β‐disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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