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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 6
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Original Articles

Reaction of 3-Diazocamphor with Silver Ion - Formation of Tricyclanone

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Pages 477-479 | Received 20 Aug 1975, Published online: 06 Dec 2006
 

Abstract

The usual method of formation of tricyclanone (1) involves thermolysis of an intimate mixture of 3-diazocamphor (3) and copper powder and is thought to involve ketocarbene (5).1 Recently this method has been supplemented2 by one which involves reaction of 3,3-dibromocamphor with diethylzinc in benzene where α-elimination to give ketocarbene (5) is mediated by 3-bromocamphor carbanion whose role is indicated by trapping as 3-bromocamphor; this material accounts for ca. 10% of product even after prolonged reaction times.

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