Rearrangements in 1,3-dipolar additions to 3,3-dimethylcycloproprene. The effect of ring strain on the rate of 1,3-dipoLar addition.
β Scribed by Donald H. Aue; Gregory S. Helwig
- Book ID
- 104234644
- Publisher
- Elsevier Science
- Year
- 1974
- Tongue
- French
- Weight
- 244 KB
- Volume
- 15
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
We have found that 1,3-dipolar additions to 3,3-dimethylcyclopropene sometimes give rearranged products, but the rearrangement products all derive from a normal 1,3-dipolar adduct.
Wo products from 3,3-dimethylcyclopropene or methylenecyclopropane' additions have been found that would correspond to a cyclopropyl to ally1 rearrangement of an intermediate in a stepwise addition.
π SIMILAR VOLUMES
With longer-chain carbonamides, partial isomerization occurs. For example, crotonamide yields 68 % a-methylsuccinimide and 19 % glutarimide. Alicyclic unsaturated carbonamides form bicyclic imides. 0 II Cyclohexenecarbonamide forms hexahydrophthalimide in 91 % yield.