Cycloaddition of Bun3P·CS2: Direct one-pot conversion of strained double bonds to 2-alkylidene-1,3-dithiolanes

✍ Scribed by R. Alan Aitken; Katriona Carcas; Lawrence Hill; Tracy Massil; Swati V. Raut

• Book ID: 104207486
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 569 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01128-3

✦ Synopsis

Reaction of the adduct between tri-n-butylphosphine and carbon disulfide 1 with norbornene gives the novel zwitterionic structure 9. In solution this dissociates to the ylide 8 which undergoes Wittig reaction with aldehydes. Using the same method, the overall conversion of the strained double bond in a variety of bicyclo[2.2, l]alkenes into 2benzylidene-1,3-dithioles 15-24 has been achieved and the reaction is also applicable to norbornadiene, affording bisdithiolanes 29-31.