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ChemInform Abstract: Addition of Thiols to α,β-Unsaturated Esters in the Presence of Alumina.

✍ Scribed by Yoshitada Suzuki; Goroh Saitoh; Satoru Nawa; Mitsuo Kodomari

Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Addition of Thiols to α,β-Unsaturated Esters in the Presence of Alumina.

-Michael-type additions of thiols to α,β-unsaturated esters in the presence of neutral alumina proceed easily under appropriate mild conditions to give the corresponding adducts [cf. (III), (VI)/(VII)] in good to excellent yields. o-Aminothiophenol (VIII) reacts selectively at the S-atom to furnish adducts (IX) in high yield. However, adducts of (VIII) with butenedicarboxylic acids are highly instable and cyclize immediately into benzothiazine derivatives [cf. (XI)].

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