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An intramolecular [8+6] cycloaddition

โœ Scribed by Ching-Yang Liu; Douglas A. Smith; K.N. Houk


Book ID
104219166
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
221 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


An intramolecular C8+61 cycloaddition

of a heptafulvene linked to a fulvene by a trimethylene chain has been observed.


๐Ÿ“œ SIMILAR VOLUMES


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In a recent article, we observed that ketiminium (1) and aldiminium (2) salts reacted with sodium bis(trimethylsilylamide) to yield products which contained aziridine rings.

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heptafulvene, 8, undergoes both an intramolecular [8+21 cycloaddition and a loll-electron electrocyclization followed by 1,5-sigmatropic hydrogen shifts to give 10 and 12, respectively. Acetylheptafulvene, 1, was reported to be unstable by Hafner,' although the reaction of 1 with DMAD to give an in