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ChemInform Abstract: Synthesis of Polycyclic Compounds Based on the Reaction of 6,6-Dimethylfulvene with Carbenes.

✍ Scribed by A. P. Molchanov; A. V. Stepakov; R. R. Kostikov

Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of Polycyclic Compounds Based on the Reaction of 6,6-Dimethylfulvene with Carbenes.

-Reaction of dimethylfulvene (I) with ethoxycarbonylcarbene, in situ obtained by copper-catalyzed destruction of ethyl diazoacetate (II), proceeds at the endocyclic double bond with cyclopropane ring formation to furnish compound (III) in good anti-selectivity. Dichlorocarbene, however, selectively attacks the exocyclic double bond opposite to the cyclopropane ring to give spirocompounds (V) and (VI). The reaction of fulvene (I) with diazomethane (VII) followed by carbene addition proceeds analogously. -(MOLCHANOV, A.

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