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The homoallyl-cyclopropylcarbinyl cation rearrangement in the acetolysis of exo- and endo-5,6-bis(methylene)-2-norbornyl p-bromobenzenesulfonates. Application of deuterium NMR spectroscopy

✍ Scribed by Ulrich Burger; Jean-Marie Sonney; Pierre Vogel

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 210 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85409-5

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✦ Synopsis

In the preceding letter we have reported on the apparently complex solvolyses of the norbornen-2-yl brosylates 1 and 2. In order to understand nore about the behaviour of hawallylic systems we have studied the acetolysis of the title cca-qzounds 2 and 4. In principle, both pair: of substrates (l/3 and 2/4) can undergo similar hcxtoallyl-cyclopropylcarbinyl rearrangewnt.

📜 SIMILAR VOLUMES

The Homoallyl-Cyclopropylcarbinyl Cation

The Homoallyl-Cyclopropylcarbinyl Cation Rearrangement in the Solvolyses of exo- and endo-5-Norbornen-2-yl p-Bromobenzenesulfonates. Application of 2H-NMR. Spectroscopy

✍ Ulrich Burger; Jean-Marie Sonney; Pierre Vogel 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 524 KB

## Abstract The buffered trifluoroethanolyses and acetolyses of __exo__‐(2‐D)‐ **(6)** and __endo__‐(2‐D)‐5‐norbornen‐2‐yl brosylates **(7)** yielded __exo__‐5‐norbornen‐2‐yl and 3‐nortricyclyl derivatives. The deuterium distribution in these products was determined unambiguously by ^2^H‐NMR. and M