Synlett

Thia-michael addition reactions using 2-[bis (alkylthio) methylene]-3-oxo-No-tolylbutanamides as odorless and efficient thiol equivalents

D Dong, H Yu, Y Ouyang, Q Liu, X Bi, Y Lu

Index: Dong, Dewen; Yu, Haifeng; Ouyang, Yan; Liu, Qun; Bi, Xihe; Lu, Yumei Synlett, 2006 , # 2 p. 283 - 287

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Citation Number: 15

Abstract

Abstract A series of 2-[bis (alkylthio) methylene]-3-oxo-No-tolylbutanamides 1 have been investigated as nonthiolic and odorless thiol equivalents in thia-Michael addition reactions. The cleavage of compounds 1 is initiated by NaOH in EtOH; the in situ generated thiolate anions undergo facile conjugate addition to α, β-unsaturated carbonyl compounds 2 affording the corresponding β-keto sulfides 3 in very high yields. Meanwhile, 3-oxo-No- ...