A Clean, Facile and Practical Synthesis of α‐Oxoketene S,S‐Acetals in Water

Abstract

A clean, facile and practical synthesis of aoxoketene S,S-acetals in water has been developed. Catalyzed by tetrabutylammonium bromide (TBAB) at room temperature in water, a range of b-dicarbonyl compounds have been converted to the corresponding a-oxoketene S,S-acetals in very high yields. The catalyst in the aqueous phase can be recycled after the separation of organic products.

[4+2] Annulation – Convenient Synthesis of Substituted Dihydropyranones in Aqueous Media

“…[17] We initially investigated the reaction of 3-[bis(methylthio)methylene]pentane-2,4-dione (1a) with benzaldehyde (2a, 2.0 equiv.) at room temperature in the presence of K 2 CO 3 (4.0 equiv.)…”

Solvent‐free Thia‐Michael Addition Reactions Using 3‐[Bis(alkylthio)methylene]pentane‐2,4‐diones as Efficient and Odorless Thiol Equivalents

“…16 It is worth noting that 1a and 1b are odorless yellowish solids and perfectly stable in open air.…”

1,3-Diketones. Synthesis and properties

“…Me 4 Me 4 2 R 2 Br, (t-Bu) 4 [61]. Cyclic thioacetals 111 were obtained using α,ω-dibromoalkanes Br(CH 2 ) n Br (Scheme 53).…”