Synthesis, stability and molecular structure of novel hydrocarbon cations consisting of a tropylium cation and two spiro[4.5]deca-2,4-dienes

Two novel hydrocarbon cations with a tropylium ion ring fused by two spiro[4,5]deca-2,4-dienes, 9 and 10 , were synthesized by a six-step sequence starting from 1,6- and 1,5-diacetyl-1,3,5-cycloheptatrienes, respectively. The p K R + values of 9 and 10 were found to be the same at 13.2, providing a...

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Bibliographic Details
Published in:Tetrahedron 2003-04, Vol.59 (16), p.2831-2841
Main Authors: Oda, Mitsunori, Kainuma, Hitoshi, Uchiyama, Takuya, Miyatake, Ryuta, Kuroda, Shigeyasu
Format: Article
Language:English
Subjects:
azulenes
carbenium ions
cyclohexanes
sprio compounds
X-ray crystal structures
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Summary:Two novel hydrocarbon cations with a tropylium ion ring fused by two spiro[4,5]deca-2,4-dienes, 9 and 10 , were synthesized by a six-step sequence starting from 1,6- and 1,5-diacetyl-1,3,5-cycloheptatrienes, respectively. The p K R + values of 9 and 10 were found to be the same at 13.2, providing a new access to highly stable cations. The density functional calculations predict that both 9 and 10 have cyclohexane rings with the chair conformation spread toward molecular edges as the most stable structure. The crystal packing and structure of 9 including dichloromethane were also elucidated by X-ray crystallographic analysis. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00369-7