BASE-INDUCED ALPHA NITRATION OF SULFONES

Sulfones are converted into their α-nitro derivatives via displacement by sulfone-stabilized carbanions on alkyl nitrates. The α-nitro sulfones are readily converted into the corresponding α-nitro-α-halo sulfones by sequential treatmentwith base and halogen or by treatment with N-halosuccinimides. Conversion of α-nitro-α-bromobutyl butyl sulfone with potassium amide in liquid ammonia into an octenesulfonamide constitutes a novel extension of the Ramberg-Bäcklund reaction. © 1969, American Chemical Society. All rights reserved.