Add time:07/11/2019         Source:sciencedirect.com

Reaction of guaiazulene (1) with methyl terephthalaldehydate (2) in methanol in the presence of hexafluorophosphoric acid at 25 °C for 2 h under aerobic conditions gives (3-guaiazulenyl)[4-(methoxycarbonyl)phenyl]methylium hexafluorophosphate (5) in 94% yield. Similarly, reactions of 1 with 2-hydroxybenzaldehyde (3) and 4-hydroxybenzaldehyde (4) under the same reaction conditions as 2 give (3-guaiazulenyl)(2-hydroxyphenyl)methylium hexafluorophosphate (6) and (3-guaiazulenyl)(4-hydroxyphenyl)methylium hexafluorophosphate (7) in 89 and 97% yields, respectively. Comparative studies on the molecular structures as well as the spectroscopic, chemical and electrochemical properties of the monocarbocation compounds 5–7 stabilized by 3-guaiazulenyl and 4-(methoxycarbonyl)phenyl (or 2-hydroxy- or 4-hydroxyphenyl) groups are reported.

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