Functionalized dienes via thermolysis of allylic sulfoxides

✍ Scribed by Ae. de Groot; B.J.M. Jansen; J.T.A. Reuvers; E.M. Tedjo

• Book ID: 104234418
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 113 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82086-4

✦ Synopsis

~wnmazy: Thermolysis of allylic sulfoxides is a useful method for the synthesis of functionalized dienes. Thermal interconversion of allylic sulfoxides and SUlfenateS, eventually followed by nucleophilic decomposition of the latter to alcohols, has found wide application in organic synthe-sis1s2. Elimination of sulfenic acid from allylic sulfoxides or sulfenates to dienes does not seem to have found much synthetic use. An example of this type of elimination is suggested by Ultee and Louw3 as an explanation of the thermolysis of 4-methylsulfinyl-1-butene and Kwart et al. 4 also mention an allylic sulfenate as a possible intermediate in the formation of butadiene