The reaction of hypochlorous acid with olefins. A convenient synthesis of allylic chlorides

✍ Scribed by Shridhar G. Hegde; Martin K. Vogel; John Saddler; Tanya Hrinyo; Ned Rockwell; Robert Haynes; Michael Oliver; Joseph Wolinsky

• Publisher: Elsevier Science
• Year: 1980
• Tongue: French
• Weight: 184 KB
• Volume: 21
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71427-4

✦ Synopsis

The reaction of HOC1 with more highly substituted olefins in methylene chloride affords allylic chlorides in 60-80% isolated yields.

The utility of the reaction is illustrated with the synthesis of Rose oxide and a-monoterpenes.

We wish to report a synthetically important reaction of hypochlorous acid with more highly substituted olefins leading to allylic chlorides rather than ch1orohydrins.l This modification n 12. The farnesol used in this work was a mixture of E and Z isomers.