Formation of 2-Methylene-1,3-oxathiole Derivatives in the Rhodium(II) Acetate-Catalyzed Reaction of α -Diazocarbonyl Compounds with Carbon Disulfide

Abstract

The rhodium(II) acetate-catalyzed reaction of α -diazocarbonyl compound with carbon disulfide gave 1,3-oxathiole-2-thione, 2-methylene-1,3-oxathiole, and 2,2′ -spirobis(1,3-oxathiole) derivatives depending on the substituent on the diazo compounds via 1,5- or 1,3-electrocyclization of thiocarbonyl ylide intermediate formed by the reaction of rhodium carbenoid with thiocarbonyl group.

Keywords:

• Diazo compound
• electrocyclization
• oxathiole
• rhodium(II)
• thiocarbonyl ylide

Dedicated to Professor Marian Mikołajczyk, CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.