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Synthesis, structure, and physical properties of 1,11-o-benzeno[2]orthocyclo[2](1,2)tropyliophane

1993; Elsevier BV; Volume: 34; Issue: 52 Linguagem: Inglês

10.1016/s0040-4039(00)61367-9

1873-3581

Yoshimasa Fukazawa, Satoshi Harada, Akira Inai, Toshiya Okajima,

Porphyrin and Phthalocyanine Chemistry

The title compound (2) has been synthesized, the structure and the physical properties of which are investigated by X-ray, spectroscopic analyses, and MO calculations. There exists charge transfer (CT) interaction between the tropylium ion and the facing phenyl ring. From the pKR+ value of 2, it can be clear that the cation 2 is stabilized by the CT interaction. In spite of the presence of bond weakening σ-π orbital mixing, the cation 2 withstands retro[4+4]type bond cleavage, which is quite interesting when compared to a facile cleavage for the congener with anthracene photodimer type structure.