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Reaction of 2‐Methylnorborn‐2‐ene with N‐Bromosuccinimide [1]
Author(s) -
Jefford C. W.,
Wojnarowski W.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530536
Subject(s) - chemistry , n bromosuccinimide , ene reaction , solvolysis , olefin fiber , norbornane , halogenation , medicinal chemistry , hydrolysis , hydroxymethyl , methylene , ozonolysis , acetone , organic chemistry , ionic bonding , catalysis , ion
The reaction of 2‐methylnorborn‐2‐ene with N‐bromosuccinimide produced exo ‐3‐bromo‐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 2‐methylenenorbornane. The hydrolysis of 2‐methyl‐3‐bromo‐nortricyclene with silver acetate in a 50% 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.