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Some reactions of 1,2,3-tribenzoylcyclopropene

✍ Scribed by Ronald Breslow; Kenneth Ehrlich; Timothy Higgs; Joseph Pecoraro; Fritz Zanker


Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
191 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis


The cyclopropenyl anion is the simplest antiaromatic system. Evidence has been accumulated' that this anion is destabilized by conjugation and strain, and that most substituted derivatives are of very high energy indeed. However, a reasonable extrapolation of substituent effects to this system suggests that compounds such as 1,2,3-tribenzoylcyclopropene (1) should have a pK, low enough to make the corresponding anion 2. accessible.


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Although reactions between (-)ephedrine E2-(S)-methylamino-l-(R)-phenylpropan-l-017 and RPOC12 (R = Cl, alkyl, aryl, alkoxy, aryloxy) can in principle afford pairs of 1,3,2-oxazaphospholanes eyimeric at phosphorus, most reports describe only one product from highly stereoselective reactions.