The reaction of guaiazulene (1) with a 0.25 molar amount of phthalaldehyde, isophthalaldehyde and terephtalaldehyde in acetic acid at room temperature (25 °C) for 4 h under argon readily gave the corresponding 3, 3'-methylenediguaiazulene having a substituent at C-α position (2, 85% yield; 3, 35%; 4, 26%; 5, 92%, respectively). The structures of these products were established on the basis of their spectroscopic (UV/VIS, IR, NMR and MS) data. A possible reaction pathway for the formation of these compounds is discussed.
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