Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Rearrangement Approaches to Cyclic Skeletons. III. Practical Route to cis-Bicyclo[4.3.0]non-4-en-7-ones Based on Photochemical [1,3] Acyl Migration of Bicyclo[3.2.2]non-6-en-2-ones
Tadao UyeharaYasuhiro KabasawaToshiaki FurutaTadahiro Kato
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1986 Volume 59 Issue 2 Pages 539-543


1-Methoxybicyclo[3.2.2]non-6-en-2-ones and the related compounds were derived I) from the Diels-Alder type 1,4-addition products of tropones with ethylene by selective reduction of the α,β-unsaturated carbonyl part (hydrosilylation followed by hydrolysis) and/or II) from bicyclo[2.2.2]oct-5-en-2-ones a) by the ring-enlargement utilizing Tieffeneau-Demjanov type conditions (1, TMS–CN; 2, LiAlH4; 3, NaNO2–AcOH) and/or b) by the related ringexpansion using trimethylsilyldiazomethane and boron trifluoride etherate. These bridged compounds were transformed into the respective [1,3] acyl migration products, cis-bicyclo[4.3.0]non-4-en-7-ones, in practical yields by direct irradiation through a Pyrex filter.

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