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 | Zendy

Goldstein Melvin J. | Zendy; Barren James P. | Zendy

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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.

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