Reactions of guaiazulene with methyl terephthalaldehydate and 2-hydroxy- and 4-hydroxybenzaldehydes in methanol in the presence of hexafluorophosphoric acid: comparative studies on molecular structures and spectroscopic, chemical and electrochemical properties of monocarbocations stabilized by 3-guaiazulenyl and phenyl groups

Abstract

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.