M. Shipman, Heidi R. Thorpe, I. Clemens
Aug 27, 1999
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron
Abstract
Abstract Two complementary approaches to 1,3,2-dioxathiolane-4-methylene-2-oxides are described. For example, treatment of 2-hydroxy-2-methylbutan-3-one with thionyl chloride (Et 3 N, CH 2 Cl 2 , −78°C) yields 5,5-dimethyl-1,3,2-dioxathiolane-4-methylene-2-oxide 5 in 58% yield. Alternatively, cyclic sulfite 11 , bearing a 4-(2-nitrophenylseleno)methyl substituent, can be induced to undergo oxidative elimination (30% H 2 O 2 , THF then CDCl 3 , Δ) to 5 in 28% yield.