The Journal of Organic Chemistry

The chemistry of sulfines. 13. 2-Thiabicyclo [2.2. 1] hept-5-ene and its S-oxides and 3-alkyl derivatives: sulfine and sulfene cyclopentadiene Diels-Alder adducts. …

E Block, A Wall

Index: Block, Eric; Wall, Alan Journal of Organic Chemistry, 1987 , vol. 52, # 5 p. 809 - 818

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Citation Number: 40

Abstract

Reaction of (trimethylsily1) methanesulfonyl chloride (6a) or-sulfonic anhydride (6b) with cesium fluoride in the presence of cyclopentadiene affords 2-thiabicyclo [2.2. lIhept-5-ene 2, a-dioxide (4) by way of sulfene CH2= S02. Similar reaction of (trimethylsily1) methanesulfinyl chloride (7) gave the unstable 2-thiabicyclo [2.2. 1] hept-5-ene endo-2- oxide (3) via the intermediacy of sulfine CH2= S0. Compound 3 can be oxidized to 4 and ...