✦ LIBER ✦
Cyclophanes, XLII. The Acid-Catalyzed Isomerization of Perhydro[2.2]paracyclophane – A Surprising Out-In Hydrogen Transfer Process
✍ Scribed by Ernst, Ludger ;Hopf, Henning ;Savinsky, Rainer
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 373 KB
- Volume
- 1997
- Category
- Article
- ISSN
- 0947-3440
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Treatment of perhydro[2.2]paracyclophane (1) with trifluoromethanesulfonic acid for 15 h at room temperature in dichloromethane results in a quantitative yield of stereoisomer 2, in which one of the bridgehead hydrogen atoms points towards the inside of the molecule (mono‐endo isomer). The constitution of 2 is derived from 2D‐NMR C,C‐INADE‐QUATE experiments and its stereochemistry from dynamic NMR experiments and molecular mechanics computations (MM3). A mechanism is suggested for the 1–2 interconversion.