β-Halo-α, β-unsaturated γ-Sultones

S Braverman, T Pechenick-Azizi, DT Major…

Index: Braverman, Samuel; Pechenick-Azizi, Tatiana; Major, Dan T.; Sprecher, Milon Journal of Organic Chemistry, 2007 , vol. 72, # 18 p. 6824 - 6831

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Citation Number: 13

Abstract

The reaction of β-iodo-α, β-unsaturated γ-sultones (ie, 4-halo-1, 2-oxathiole 2, 2-dioxides) in aprotic polar solvents such as DMSO or acetone, with'soft'nucleophiles such as iodide or thioacetate, yields an allenesulfonate by a very facile halophilic ring-opening E2-elimination. The'harder'nucleophile, azide ion, reacts under the same conditions to yield the corresponding β-azido-α, β-unsaturated γ-sultone (ie, 4-azido-1, 2-oxathiole 2, 2-dioxide), ...