Silver Ion Induced Rearrangement of N-Chloramines. Isolation of an Ionic Product in High Yield

Article abstract of DOI:10.1021/jo01308a033

Treatment of N-chlorogranatanine with silver tetrafluoroborate in benzene followed by hydride reduction provides δ-coniceine in high yield. Similarly, N-chloro derivatives of nortropane and trans-decahydroquinoline provided pyrrolizidine and 1-azabicyclo<5.3.0>decane, respectively. Under these reaction conditions, only small amounts of secondary amines are found in the product. The rearrangement product of N-chlorogranatanine was isolated without hydride reduction and shown to be the expected immonium ion product.