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Synthesis of anti ‐9‐Bromo‐ and anti ‐9‐Chlorobicyclo[4.2.1]nonatriene via Bicyclo[4.2.1]nonatriene→Bicyclo[4.2.1]nonatriene Rearrangement
Author(s) -
Goldstein Melvin J.,
Barren James P.
Publication year - 1986
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.19860690304
Subject(s) - bicyclic molecule , chemistry , stereoselectivity , yield (engineering) , bromide , derivative (finance) , stereochemistry , organic chemistry , materials science , economics , financial economics , metallurgy , catalysis
The first syntheses of 9‐bromo‐ and 9‐chlorobicyclo[4.2.1]nona‐2,4,6‐trienes were each achieved in three stereoselective steps from the 9,9‐bis(selenophenyl) derivative 9 in 79% overall yield for the bromide and 64% for the chloride. A deuterium‐labeling experiment reveals the first rearrangement of a bicyclo[4.2.1]nonatriene which leaves the ring system intact.