Acetolysis of 4-bromobutyl-1,1-d2 p-nitrobenzenesulfonate. Evidence for 1,4-bromine participation and the existence of a 5-membered cyclic bromonium ion during acetolysis.

✍ Scribed by Walter S. Trahanovsky; G.Leroy Smyser; Michael P. Doyle

• Book ID: 104222760
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 198 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89569-6

✦ Synopsis

We wish to report that acetolysis of 4-bromobutyl-1,1-d, p-nitrobenzenesulfonate leads to 78% of the unrearranged product, 4-bromobutyl-l,l-& acetate, and 22$ of the rearranged product, 4-bromobutyl-4,4-h acetate.