Zur Reaktion von Pinenen mit Chlorwasserstoff

✍ Scribed by Weigand, Eckehard F. ;Schneider, Hans-Jörg

• Publisher: Wiley (John Wiley & Sons)
• Year: 1979
• Tongue: English
• Weight: 164 KB
• Volume: 112
• Category: Article
• ISSN: 0009-2940
• DOI: 10.1002/cber.19791120826

✦ Synopsis

On the Reaction of Hydrogen Chloride with Pinenes

syn‐Addition of DCI to the less hindered site of α‐ and β‐pinene (1, 2) is demonstrated by a combination of 13C‐ and 2H‐NMR spectroscopy. The resulting tertiary chloride is configurationally pure and isomerizes to bornyl chloride only. The rapidity of the isomerization with the possible conversion of a tertiary to a secondary carbocation is rationalized by strain calculations with a molecular mechanics force field.