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Reaction of 2-Methylnorborn-2-ene with N-Bromosuccinimide [1]

✍ Scribed by C. W. Jefford; W. Wojnarowski

Publisher
John Wiley and Sons
Year
1970
Tongue
German
Weight
654 KB
Volume
53
Category
Article
ISSN
0018-019X

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✦ Synopsis

The reaction of 2-methylnorborn-2-ene with N-bromosuccinimide produced exo-3bromo-2-methylenenorbornane and 2-methyl-3-bromonortricyclene in a 3 : 1 ratio. No 2-bromomethyl-norborn-2-ene was found. Most of the unreacted olefin was found to be isomerized to 2methylenenorbornane.

The hydrolysis of 2-methyl-3-bromo-nortricyclene with silver acetate in a 50 yo mixture of acetone and water afforded the corresponding alcohol and acetate. Exo-3-bromo-2-methylenenorbornane on similar treatment gave the exo-3-hydroxy-2-methylene-norbornane and 2-hydroxymethyl-norbornane and 2-hydroxymethyl-norborn-2-ene and their corresponding acetates in a 3: 2 ratio.

An ionic rather than a radical mechanism is proposed for the bromination reaction. In the solvolysis reactions of the resulting bromides the nature of the ionic intermediates is discussed.

📜 SIMILAR VOLUMES

Reaction of 2-Methylenenorbornane with N
Reaction of 2-Methylenenorbornane with N-Bromosuccinimide
✍ C. W. Jefford; W. Wojnarowski 📂 Article 📅 1972 🏛 John Wiley and Sons 🌐 German ⚖ 610 KB

## Abstract The reaction of 2‐methylenenorbornane with N‐bromosuccinimide produced a mixture of six monobromides in an overall yield of about 60%. By irradiation in the presence of benzoyl peroxide __exo__‐ and __endo__‐3‐bromo‐2‐methylenenorbornanes, 2‐bromomethylnorborn‐2‐ene, __Z__‐ and __E__‐2‐

Reaction of Singlet Oxygen with 2-Methyl
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✍ Charles W. Jefford; André F. Boschung 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 963 KB

## Abstract The dye‐sensitized photo‐oxygenation of 2‐methylnorbonr‐2‐ene (**3**), 2‐methylidene‐norbornane (**4**) and their 7,7‐dimethyl derivatives (**5** and **6**) has been studied. In all cases allylically rearranged hydroperoxides were formed, except that **4** also gave a little norbornanon