𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Reaction of 2-Methylenenorbornane with N-Bromosuccinimide

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

Publisher
John Wiley and Sons
Year
1972
Tongue
German
Weight
610 KB
Volume
55
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

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‐bromomethylenenorbornanes and 1‐bromomethylnortricyclene were found in a percentage ratio of 43.0, 7.5, 6.5, 19.0, 19.0 and 5.0. Without benzoyl peroxide, in the dark, the same products were obtained, but in a percentage ratio of 23.0, 3.0, 17.0, 26.0, 26.0 and 7.0. These results are rationalized in terms of an ionic mechanism in concurrence with some radical mechanism contribution.

📜 SIMILAR VOLUMES

Reaction of 2-Methylnorborn-2-ene with N
Reaction of 2-Methylnorborn-2-ene with N-Bromosuccinimide [1]
✍ C. W. Jefford; W. Wojnarowski 📂 Article 📅 1970 🏛 John Wiley and Sons 🌐 German ⚖ 654 KB

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-