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Issue 9, 2001
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Rhodium(II)-carbenoid C–H insertion reactions in the synthesis of α,β′-dioxospirane systems

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Abstract

Spiro[4.4]nonane-, spiro[4.5]decane- and spiro[4.6]undecane-α,β′-diones have been prepared from 1-diazo-4-(2,2-ethylenedioxycycloalkan-1-yl)butan-2-one intermediates by Rh2(OAc)4- and Rh2(TPA)4-catalyzed C–H insertions. Competitive insertions also gave trans-bicyclic derivatives. The relative stereochemistry in bicyclic derivatives has been determined by single crystal X-ray analyses.

Graphical abstract: Rhodium(II)-carbenoid C–H insertion reactions in the synthesis of α,β′-dioxospirane systems

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Supplementary files

Article information


Submitted
02 Jan 2001
Accepted
14 Mar 2001
First published
10 Apr 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1024-1029
Article type
Paper

Rhodium(II)-carbenoid C–H insertion reactions in the synthesis of α,β′-dioxospirane systems

P. S. Aburel, C. Rømming and K. Undheim, J. Chem. Soc., Perkin Trans. 1, 2001, 1024
DOI: 10.1039/B100179P

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