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Thermal rearrangement of 3,6-dimethylidene-1,7-octadiene. An intramolecular cycloaddition reaction

✍ Scribed by Kenneth J. Shea; Sean Wise

Book ID
104242670
Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
185 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

Thermal n2 + n2 cycloaddition reactions leading to four-membered rings are orbital symmetry allowed when they proceed via a single inversion pathway at one of the reacting centers.

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## Abstract The tricyclic lactams 4a–h, possessing a bicyclo[2.2.2]octadiene moiety, obtained by intramolecular Diels‐Alder reaction of the vinylidene malondiamides 1a–h, generally isomerize in boiling xylene to give the new lactams 7a–h, now bearing a bicyclo[3.2.1]octadiene part. The difference i