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38
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3042833799
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note
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At 45 °C we could measure a 65% de from the NMR spectra on the crude product, but the proportion of amino sulfoxides in the mixture was lower than 60%.
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40
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3042752458
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note
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The authors have deposited atomic coordinates for 15B with the Cambridge Crystallographic Data Centre (Deposit No. 218989). The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
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41
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0642309145
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Lopez Sastre, J.A.5
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42
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3042840729
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note
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Their NMR spectra suggested that the sulfoxides had been reduced into thioethers and the N-S bond partially hydrolyzed. These results are similar to those previously obtained from the adducts resulting from reactions of N-sulfinyl aldimines (ref 9).
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43
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3042747874
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note
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Diastereoisomers 16A and 16B differ in the configuration at sulfinylated carbon, whereas 17B and 16A have different sulfur configuration, which allows to have information about the influence of all the chiral centers.
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45
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2142858450
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46
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3042752457
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note
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3 interaction, presumably small due to the long S-O bond (see Scheme 7), the observed slightly lower reactivity of 27 is not surprising.
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47
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3042829188
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note
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To check the possible evolution through the four membered σ-sulfurane intermediates, we have prepared the N-sulfonyl aminosulfoxide 31, unable to form the six membered σ-sulfuranes, by reaction of the N-sulfonylimine derived from benzophenone with racemic methyl p-tolyl sulfoxide in the presence of LDA. The reaction of 31 with TFAA (5 equiv) and sym-collidine (4 equiv) under the same experimental conditions used for carbamates did not evolve into the amino alcohol derivative 33 but yielded the aldehyde 34, resulting in a normal Pummerer reaction. As the acidity of the NH group at 32 is higher than that of any carbamate, the fact that this substrate does not undergo the non-oxidative Pummerer reaction suggests that these reactions evolve through a six membered σ-sulfuranes as intermediates (instead of a four membered σ-sulfuranes), only possible for carbamates. However, the observed evolution for 31 could be due to the lower reactivity of the N-sulfonylamides.
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48
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0035015052
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N-Sulfonylimine was prepared following the procedure described in the following reference: Ram, R. N.; Khan, A. A. Synth. Commun. 2001, 31, 841.
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Ram, R.N.1
Khan, A.A.2
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