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85027965918
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Cyclobutanones la-d were readily prepared by [2 + 2] cycloaddition of the corresponding allylic ethers with dichloroketene and the subsequent dechlorination with zinc
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Cyclobutanones la-d were readily prepared by [2 + 2] cycloaddition of the corresponding allylic ethers with dichloroketene and the subsequent dechlorination with zinc.
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26
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85027980794
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2
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2.
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27
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4544359160
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The details of the syntheses and crystal structures will be reported separately
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J. Chem. Soc. A
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Green, A.1
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Taylor, S.H.3
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28
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85028018282
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Monitoring the reaction by capillary GC revealed that decarbonylated cyclopropane 8a was formed as a sole side product (~4.5%), and formation of cyclopentanone 7a was not observed
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Monitoring the reaction by capillary GC revealed that decarbonylated cyclopropane 8a was formed as a sole side product (~4.5%), and formation of cyclopentanone 7a was not observed.
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29
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85027966694
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Whereas a less substituted a-bond is cleaved in the hydrogenolysis of an ordinary cyclobutanone.4b the more substituted a-bond is cleaved in the present case. It is likely that coordination of the ether linkage to rhodium facilitates insertion into the more substituted but proximate a-bond
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Whereas a less substituted a-bond is cleaved in the hydrogenolysis of an ordinary cyclobutanone.4b the more substituted a-bond is cleaved in the present case. It is likely that coordination of the ether linkage to rhodium facilitates insertion into the more substituted but proximate a-bond.
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31
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85027965923
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Decarbonylated cyclopropane 8a was observed by GC as the only side product (~12%)
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Decarbonylated cyclopropane 8a was observed by GC as the only side product (~12%).
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32
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33847085217
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Campbell, R. E. Jr.; Lochow, C. F.; Vora, K. P.; Miller, R. G. J. Am. Chem. Soc. 1980, 102, 5824.
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Vora, K.P.3
Miller, R.G.4
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33644594303
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Evans, I. A.; Russell, D. R.; Bright, A.; Shaw, B. L. Chem. Commun. 1971, 841.
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, pp. 841
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Evans, I.A.1
Russell, D.R.2
Bright, A.3
Shaw, B.L.4
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85027996755
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Alternatively, recyclization of 4 by addition of the Rh-C linkage across the C—C double bond in a 5-endo mode followed by reductive elimination forming a C-O bond is also conceivable for the production of 7a
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Alternatively, recyclization of 4 by addition of the Rh-C linkage across the C—C double bond in a 5-endo mode followed by reductive elimination forming a C-O bond is also conceivable for the production of 7a.
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35
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85028000120
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Neither 5a nor 7a was detected by GC
-
Neither 5a nor 7a was detected by GC.
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36
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85027987709
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The reaction of lb catalyzed by the dppb complex 2c afforded the corresponding decarbonylated cyclopropane 8b in 93% yield, being in accordance with other examples
-
The reaction of lb catalyzed by the dppb complex 2c afforded the corresponding decarbonylated cyclopropane 8b in 93% yield, being in accordance with other examples.
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