The crystal structure and characteristic chemical property of 1,2-bis(3-guaiazulenylmethylium)benzene bishexafluorophosphate

Reaction of guaiazulene ( 1 ) with a 0.5 molar amount of phthalaldehyde in a mixed solvent of acetonitrile and diethyl ether in the presence of hexafluorophosphoric acid at 25°C under aerobic conditions rapidly gives the title dicarbocation compound, 1,2-bis(3-guaiazulenylmethylium)benzene bishexafl...

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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 2; pp. 275 - 279
Main Authors Sasaki, Masato, Nakamura, Masaru, Hannita, Gen, Takekuma, Hideko, Minematsu, Toshie, Yoshihara, Masakuni, Takekuma, Shin-ichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.2003
Elsevier
Subjects
azulenes
carbonium ions
Chemistry
Chemistry, Organic
Physical Sciences
reduction
Science & Technology
X-ray crystal structures
X-ray crystal structures
carbonium ions
reduction
azulenes
azalenes
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Summary:Reaction of guaiazulene ( 1 ) with a 0.5 molar amount of phthalaldehyde in a mixed solvent of acetonitrile and diethyl ether in the presence of hexafluorophosphoric acid at 25°C under aerobic conditions rapidly gives the title dicarbocation compound, 1,2-bis(3-guaiazulenylmethylium)benzene bishexafluoro-phosphate ( 2 ) in 98% yield. Reduction of 2 with a large excess of NaBH 4 in a mixed solvent of acetonitrile and ethanol at 25°C quantitatively affords a unique intra-molecular cycloaddition compound 9 via the intermediate 8 . The crystal structure and characteristic chemical property of 2 are reported. The crystal structure and characteristic chemical property of the title dicarbocation compound are reported in detail.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02560-1