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Synthese und Hydrolyse von 6‐ exo ‐substituierten 2‐Methyl‐2‐ exo ‐norbornyl und 2‐Methyl‐2‐ endo ‐norbornyl‐(2,4‐dinitrophenyl)äthern Norbornane. 16. Mitteilung
Author(s) -
Grob Cyril A.,
Von Sprecher Georg,
Waldner Adrian
Publication year - 1983
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.19830660834
Subject(s) - 2 norbornyl cation , chemistry , norbornane , hydrolysis , stereochemistry , medicinal chemistry , yield (engineering) , organic chemistry , materials science , metallurgy
The Synthesis and Hydrolysis of 6‐ exo ‐Substituted 2‐Methyl‐2‐ exo ‐norbornyl and 2‐Methyl‐2‐ endo ‐norbornyl 2,4‐Dinitrophenyl Ethers The synthesis of the title compounds and their hydrolysis products in aqueous dioxane are described. Upon hydrolysis, the 2‐ exo ‐ethers 1 (X=N 2 phO) as well as the 2‐ endo ‐ethers 2 (X=N 2 phO) yield the corresponding 2‐methyl‐2‐ exo ‐norbornanols 3 only. Therefore, the 2‐ exo ‐ethers react with retention of configuration at C(2), the 2‐ endo ‐ethers 2 with inversion at C(2).