Substituent effects in the reaction of allyl trichloroacetimidates with N-halosuccinimides: Cyclization vs aza-Claisen rearrangement

✍ Scribed by Hossein Shabany; Christopher D. Spilling

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 239 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)10837-1

✦ Synopsis

We report a novel substituent effect in the reaction of allylic triehtoroacetimidates with N-halosuccinimides. Reaction ofE allylic trichloroacetimidates bearing phosphonate or cyano substituents with N-BS in CHCl3 results in a [3.3] sigmatropic rearrangement. In contrast, the Z allylic phosphonate or phenyl substituted allylic trichloroacotimidate undergo halocyclization,