Reaction of 3-Diazocamphor with Silver Ion - Formation of Tricyclanone |
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| Authors: | Frances C Brown David G Morris A Malcolm Murray |
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| Institution: | Department of Chemistry , University of Glasgow , Glasgow, G12 8QQ |
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| 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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