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. Author manuscript; available in PMC: 2009 Nov 7.
Published in final edited form as: J Org Chem. 2008 Oct 10;73(21):8669–8672. doi: 10.1021/jo8017389

Table 2.

Reaction of imine 2 with p-cresol.agraphic file with name nihms-86404-t0003.jpg

entry aqueous buffer yieldb (%)
1 200 mM NaH2PO4, pH 5 37
2 200 mM NaH2PO4-Na2HPO4, pH 6.0 35
3 200 mM NaH2PO4-Na2HPO4, pH 7.0 32
4 200 mM NaH2PO4-Na2HPO4, pH 8.0 26
5 200 mM Na2HPO4, pH 9 22
6 100 mM Tris, pH 8.0 25
7c 100 mM NaH2PO4-Na2HPO4, pH 7 [68]
a

Imine 2 (95 mM) and p-cresol (25 mM) at 23 °C for 24 h.

b

Determined by 1H NMR of the extracted mixture. For entries 1-6, yield of di-addition product was <5%. Percentage of modified ortho positions of the phenolic OH of p-cresol is indicated in bracket; complete conversion to the di-addition product = 200% in bracket.

c

Imine 2 (50 mM) and p-cresol (10 mM) in the buffer prepared with D2O (no DMSO was added) at 37 °C for 24 h.