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An Unusual Rearrangement and its Dependence on Configuration
Author(s) -
Zimmerman Howard E.,
Wang Pengfei
Publication year - 2001
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 - 10.1002/1522-2675(20010613)84:6<1342::aid-hlca1342>3.0.co;2-w
Subject(s) - chemistry , moiety , rearrangement reaction , cope rearrangement , stereochemistry , carroll rearrangement , sigmatropic reaction , catalysis , organic chemistry
In the course of a synthetic study, we encountered an unusual rearrangement that we now report, one that involves a 5‐nitronorbornenyl system having 7‐ endo‐ and 7‐ exo ‐pyridin‐2‐yl groups being treated under Nef ‐reaction conditions. The stereoisomers differ in their Nef ‐reaction behavior: the isomer with the pyridin‐2‐yl group exo to the NO 2 moiety primarily affords the Nef reaction, however, with formation of a rather unusual rearrangement side‐product. The endo‐ pyridyl stereoisomer proceeded exclusively with rearrangement.