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33746280442
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note
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The remainder of the material was starting material 1 or rearranged allylcyclopropylbenzylamine.
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20
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33746310837
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b) J. Weber, U. Haslinger, U. H. Brinker, J. Org. Chem. 1999, 64, 6084-6086.
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33746322959
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25
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0001601276
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e) M. Pomerantz, R. N. Wilke, G. W. Gruber, U. Roy, J. Am. Chem. Soc. 1972, 94, 2752-2758.
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29
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33746271240
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note
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The structure of 5 was assigned based on the X-ray analysis of the ketoaldehyde derived from cleavage of the cyclobutene ring.
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30
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33746283266
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note
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The relative stereochemistry of 12 was assigned based on NOESY analysis.
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31
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33746300724
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note
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A steric argument was used to rationalize the selectivity of the ene versus [2+2] pathway for simple bicyclo[1.1.0]butanes (see reference [12]); prior pericyclic reactions of bicyclo[1.1.0]butanes were limited to structurally simple substrates, and no further synthetic applications were reported.
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32
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33746308295
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note
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Reaction of 3-phenylbicyclo[1.1.0]butyllithium with acetaldehyde or benzaldehyde followed by phase-transfer alkylation resulted in a low yield of the alkylated product.
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33
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0346046471
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For a demonstration of the radical nature of reactions of bicyclo[2.1.0]pentane with alkenes, see: a) P. G. Gassman, K. T. Mansfield, T. J. Murphy, J. Am. Chem. Soc. 1969, 91, 1684-1689;
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Gassman, P.G.1
Mansfield, K.T.2
Murphy, T.J.3
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35
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0037165747
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J. P. Stevenson, W. F. Jackson, J. M. Tanko, J. Am. Chem. Soc. 2002, 124, 4271-4281.
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Stevenson, J.P.1
Jackson, W.F.2
Tanko, J.M.3
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36
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0000134041
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a) T. Linker, Angew. Chem. 1997, 109, 2150-2152;
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Linker, T.1
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38
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33746296104
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note
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b) alkene Z/E isomerization during N-alkylation was not responsible for the lack of stereospecificity; (Z)-cinnamyl bromide when treated with N-(3-phenylprop-2-ynyl)diphenylphosphinylamide gives an alkylated product with an intact Z double-bond configuration in 67% yield.
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