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0042938853
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note
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2000-2001 American Chemical Society Division of Organic Chemistry Graduate Fellow, sponsored by DuPont Pharmaceuticals, Inc.
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3
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33746873936
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Martínez, A.G.1
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Rodríguez, E.5
Martínez, P.6
Subramanian, L.R.7
Gancedo, A.G.8
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31
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0030220976
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Ozonolysis of the hydrochloric salt of the corresponding free amine has been reported to proceed normally in quantitative yield. Martínez, A. G.; Teso, E.; García, A.; de la Moya, S.; Martínez, P.; Subramanian, L. R. Tetrahedron: Asymmetry 1996, 7, 2177-2180.
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Martínez, A.G.1
Teso, E.2
García, A.3
De La Moya, S.4
Martínez, P.5
Subramanian, L.R.6
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0042908644
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note
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The rest of the material (50%) is the hydroxycyclobutanone 3.
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33
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0000221391
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Prepared by isomerization of the tert-butyldimethylsilyl ether of the E-isomer with iodine and light (to give a 4:3 E to Z ratio) followed by desilylation and separation. It is interesting that Wittig olefination of the corresponding cyclobutanone (prepared from the silyl enol ether of 2-methylcyclopentanone by addition of ethyl propiolate, conversion of the ester to the aldehyde, Baeyer-Villiger oxidation, and hydrolysis) gave only the E-isomer of the alkene, even at high temperatures, in contrast to the work of Still. Sreekumar, C.; Darst, K. P.; Still, W. C. J. Org. Chem. 1980, 45, 4260.
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J. Org. Chem.
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Sreekumar, C.1
Darst, K.P.2
Still, W.C.3
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It is interesting to note that the hydroxycyclobutanone 3 exists in solution as an equilibrium mixture of 3 and the hydroxyketone 21 in a 2:1 ratio, (a) Harding, K. E.; Trotter, J. W.; May, L. M. J. Org. Chem. 1977, 42, 2715-2719.
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(1977)
J. Org. Chem.
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Harding, K.E.1
Trotter, J.W.2
May, L.M.3
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