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Thermal rearrangement of anti-9-methyl-cis-bicyclo[6.1.0]nonatriene and syn-9-methyl-cis-bicyclo[6.1.0]nonatriene

✍ Scribed by Radlick, Phillip; Fenical, William


Book ID
127372314
Publisher
American Chemical Society
Year
1969
Tongue
English
Weight
359 KB
Volume
91
Category
Article
ISSN
0002-7863

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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