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(+)-Binol loading was limited to 10%, as above that amount the reaction became extremely viscous and no further acceleration was observed
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(+)-Binol loading was limited to 10%, as above that amount the reaction became extremely viscous and no further acceleration was observed.
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23
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85034202349
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note
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3 compared to earlier rate studies is because reactions are no longer being diluted with 100 μL of MeCN. In addition, more accurate measurements are now being made. We are currently obtaining five different samples from a single reaction and analyzing them. This was not practical in the initial stages when a very large number of different reactions were conducted.
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24
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85034183590
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It had previously been shown that 10 mol % MeOH results in a 1.5-fold rate enhancement. No further tests were conducted. See ref 10.
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It had previously been shown that 10 mol % MeOH results in a 1.5-fold rate enhancement. No further tests were conducted. See ref 10.
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26
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85034200956
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For reaction of cyclohexanecarboxaldehyde with methyl acrylate see ref 7. No yield was given, but the half-life for the reaction using 20 mol % DABCO was 10 days.
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For reaction of cyclohexanecarboxaldehyde with methyl acrylate see ref 7. No yield was given, but the half-life for the reaction using 20 mol % DABCO was 10 days.
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27
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17144397289
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For reaction of anisaldehyde with methyl acrylate, see: Foucaud, A.; El Guemmout, F. Bull. Chim. Soc. Fr. 1989, 403-408. They reported 90% yield after 20 days using 15 mol % DABCO.
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Foucaud, A.1
El Guemmout, F.2
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28
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85034187898
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Methyl acrylate has a tendency to dimerize, and with less reactive acceptors this is the major product (see refs 29 and 30). Under our optimum conditions, the rate of reaction with the aldehyde is enhanced relative to dimerization.
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Methyl acrylate has a tendency to dimerize, and with less reactive acceptors this is the major product (see refs 29 and 30). Under our optimum conditions, the rate of reaction with the aldehyde is enhanced relative to dimerization.
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29
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0001550073
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