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The ring closure of 5-methylcyclopenta-1,3-dien-5-ylcarbene to 1-methylbenzvalene. An intramolecular 1,4 cheletropic carbene addition

✍ Scribed by Ulrich Burger; Gérard Gandillon

Book ID: 104237932
Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 180 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86566-7

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✦ Synopsis

The title carbene (1) is shown to produce the benzvalene skeleton by stereospecific intramolecular 1,4 addition and not by classic cyclopropanation. Cyclopentadienylanion (1) reacts with chlorocarbene generated from dichloromethane and methyl lithium to give benzvalene (4).' Analogous reactions have been reported for further carbo-and heteroaromatic anions.' Mechanistic studies in our laboratory suggest that the parent reaction proceeds uia the cyclopentadienylcarbene (2).

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