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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

✍ Scribed by Melvin J. Goldstein; James P. Barren

Publisher
John Wiley and Sons
Year
1986
Tongue
German
Weight
458 KB
Volume
69
Category
Article
ISSN
0018-019X

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✦ Synopsis

The first syntheses of 9-bromo-and 9-chlorobicyclo[4.2.l]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. llnonatriene which leaves the ring system intact.

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