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pKa phenol = 9.9 pKa2 of carbonic acid = 10.33 - PowerPoint PPT Presentation


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Chandrasekhar, S.; Basu , Debjit ; Sailu , M.; Kotamraju , S. Novel synthetic route to the tricyclic core of ()- galanthamine . Tetrahedron Letters (2009), 50(34), 4882-4884. . pKa phenol = 9.9 pKa2 of carbonic acid = 10.33.

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Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34), 4882-4884.


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pKa phenol = 9.9

pKa2 of carbonic acid = 10.33


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The ClaisenRearrangment is a [3,3] sigmatropic rearrangement

Aromatic Claisen Rearrangement

Cope Rearrangement is related


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Sigmatropic: One sigma bond is changed to another.


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pKa conjugate acid of imidazole = 7.2


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DIPEA = Diisopropylethylamine (Hunig’s Base). This base is more sterically hindered, and thus less nucleophilic, than triethylamine.

pKa of the conjugate acid of Hunig’s base = 11.0

MOM = Methoxymethyl

MOMCl = H3C-O-CH2-Cl


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2,6-Lutidine =

pKa conjugate acid of 2,6-lutidine = 6.7


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pKa hydroxylamine hydrochloride = 6

pKa conjugate acid of pyridine = 5.2

pKa conjugate acid of triethylamine = 10.6


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pKaacetonitrile = 25

pKaphenylacetonitrile = 22

DMPU = Dimethylpropyleneurea = solvent to replace HMPA, a carcinogen

LDA = lithium diisopropylamide

pKa of diisopropylamine(conjugate acid of LDA) = 36


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pKa p-toluenesulfonic acid = - 0.4


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DPPA = diphenylphosphorylazide =

DBU = Diazabicycloundecene =

Conjugate acid of DBU pKa = 13.2


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